N-(32-amino-3,6,9,12,15,18,21,24,27,30-decaoxadotriacontyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide → HCID 86699385, compound

HRID 45749Notes

Reaction equation

HRID 45749 reaction equation
[C:1]([O:42]N1C(=O)CCC1=O)(=O)[CH2:2][CH2:3][O:4][CH2:5][CH2:6][O:7][CH2:8][CH2:9][O:10][CH2:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH2:17][CH2:18][O:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH2:29][CH2:30][C:31]([O:33]N1C(=O)CCC1=O)=O.[NH2:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][CH2:73][O:74][CH2:75][CH2:76][O:77][CH2:78][CH2:79][O:80][CH2:81][CH2:82][NH:83][S:84]([C:87]1[CH:92]=[CH:91][CH:90]=[C:89]([CH:93]2[C:102]3[C:97](=[C:98]([Cl:104])[CH:99]=[C:100]([Cl:103])[CH:101]=3)[CH2:96][N:95]([CH3:105])[CH2:94]2)[CH:88]=1)(=[O:86])=[O:85]>>[Cl:103][C:100]1[CH:101]=[C:102]2[C:97](=[C:98]([Cl:104])[CH:99]=1)[CH2:96][N:95]([CH3:105])[CH2:94][CH:93]2[C:89]1[CH:88]=[C:87]([S:84]([NH:83][CH2:82][CH2:81][O:80][CH2:79][CH2:78][O:77][CH2:76][CH2:75][O:74][CH2:73][CH2:72][O:71][CH2:70][CH2:69][O:68][CH2:67][CH2:66][O:65][CH2:64][CH2:63][O:62][CH2:61][CH2:60][O:59][CH2:58][CH2:57][O:56][CH2:55][CH2:54][O:53][CH2:52][CH2:51][NH:50][C:31](=[O:33])[CH2:30][CH2:29][O:28][CH2:27][CH2:26][O:25][CH2:24][CH2:23][O:22][CH2:21][CH2:20][O:19][CH2:18][CH2:17][O:16][CH2:15][CH2:14][O:13][CH2:12][CH2:11][O:10][CH2:9][CH2:8][O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][C:1]([NH:50][CH2:51][CH2:52][O:53][CH2:54][CH2:55][O:56][CH2:57][CH2:58][O:59][CH2:60][CH2:61][O:62][CH2:63][CH2:64][O:65][CH2:66][CH2:67][O:68][CH2:69][CH2:70][O:71][CH2:72][CH2:73][O:74][CH2:75][CH2:76][O:77][CH2:78][CH2:79][O:80][CH2:81][CH2:82][NH:83][S:84]([C:87]2[CH:92]=[CH:91][CH:90]=[C:89]([CH:93]3[C:102]4[C:97](=[C:98]([Cl:104])[CH:99]=[C:100]([Cl:103])[CH:101]=4)[CH2:96][N:95]([CH3:105])[CH2:94]3)[CH:88]=2)(=[O:86])=[O:85])=[O:42])(=[O:86])=[O:85])[CH:92]=[CH:91][CH:90]=1

Participants

3

Reactant 2

HCID 67457976N-(32-amino-3,6,9,12,15,18,21,24,27,30-decaoxadotriacontyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide2×HCID 77078480Bis-PEG9-NHS ester

Product 1

HCID 86699385HCID 86699385, compoundYield 49.8%

Procedure

Compound 217 was prepared following the procedure outlined in Example 168 using bis(2,5-dioxopyrrolidin-1-yl) 4,7,10,13,16,19,22,25,28-nonaoxahentriacontane-1,31-dioate (69.1 mg, 0.0975 mmol) and N-(32-amino-3,6,9,12,15,18,21,24,27,30-decaoxadotriacontyl)-3-(6,8-dichloro-2-methyl-1,2,3,4-tetrahydroisoquinolin-4-yl)benzenesulfonamide (Compound 214, 166.2 mg, 0.195 mmol). Purification by preparative HPLC gave the title compound (106.3 mg) as a TFA salt. 1H-NMR (400 MHz, CD3OD): δ 7.88 (d, 2H), 7.76 (s, 2H), 7.66 (t, 2H), 7.56 (m, 4H), 6.86 (s, 2H), 3.90 (m, 2H), 3.82 (t, 2H), 3.76 (m, 6H), 3.62-3.41 (m, 28H), 3.38 (m, 6H), 3.35-3.28 (m, 56H), 3.15 (s, 6H), 3.05 (t, 4H), 2.43 (t, 4H). MS (m/z): 1094.37 [(M+2H)/2]+.

Workup

  1. customCompound 217 was prepared
  2. customPurification by preparative HPLC

Sources & evidence

ORD record
ord-60afc9540e8d4868b20b1ec9d6772bb8
Source dataset
uspto-grants-2013_09
Patent number
US08541448B2

Reaction notes

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