Diisopropylethylamine → HCID 89720659, compound

HRID 63749Notes

Reaction equation

HRID 63749 reaction equation
OC(C(F)(F)F)=O.[NH2:8][CH2:9][C:10]1[CH:40]=[C:39]([F:41])[C:13]([C:14]([NH:16][C@@H:17]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([C:28]3[C:29](=[O:38])[N:30]([CH3:37])[C:31](=[O:36])[N:32]([CH3:35])[C:33]=3[CH3:34])=[CH:24][CH:23]=2)[C:18]([OH:20])=[O:19])=[O:15])=[C:12]([F:42])[CH:11]=1.O=C1CCC(=O)N1[O:50][C:51](=O)[CH2:52][CH2:53][O:54][CH2:55][CH2:56][O:57][CH2:58][CH2:59][O:60][CH2:61][CH2:62][O:63][CH2:64][CH2:65][NH:66][C:67](=[O:77])[CH2:68][CH2:69][N:70]1[C:74](=[O:75])[CH:73]=[CH:72][C:71]1=[O:76].CCN(C(C)C)C(C)C>>[O:76]=[C:71]1[CH:72]=[CH:73][C:74](=[O:75])[N:70]1[CH2:69][CH2:68][C:67]([NH:66][CH2:65][CH2:64][O:63][CH2:62][CH2:61][O:60][CH2:59][CH2:58][O:57][CH2:56][CH2:55][O:54][CH2:53][CH2:52][C:51]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([F:42])[C:13]([C:14]([NH:16][C@@H:17]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([C:28]3[C:29](=[O:38])[N:30]([CH3:37])[C:31](=[O:36])[N:32]([CH3:35])[C:33]=3[CH3:34])=[CH:26][CH:27]=2)[C:18]([OH:20])=[O:19])=[O:15])=[C:39]([F:41])[CH:40]=1)=[O:50])=[O:77]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 513409501-Maleinimido-3-oxo-7,10,13,16-tetraoxa-4-azanonadecan-19-oic acid succinimidyl esterHCID 117833840HCID 117833840, compound

Product 1

HCID 89720659HCID 89720659, compound

Procedure

The title compound was prepared using a similar procedure as described in Example 1, Step 11, starting from (S)-2-(4-aminomethyl-2,6-difluorobenzoylamino)-3-[4-(1,3,6-trimethyl-2,4-dioxo-1,2,3,4-tetrahydropyrimidin-5-yl)phenyl]propionic acid TFA salt (120 mg, 0.2 mmol), 3-[2-[2-[2-[2-[3-(2,5-dioxo-2,5-dihydro-pyrrol-1-yl)-propionylamino]ethoxy]ethoxy]ethoxy]ethoxy]propionic acid-2,5-dioxo-pyrrolidin-1-yl ester (103 mg, 0.2 mmol), and DIPEA (129 mg, 174 uL, 1.0 mmol), and after HPLC purification, resulted in a white solid (75 mg, 43%). ES(+)-HRMS m/e calcd. for C42H50F2N6O13 (M+Na)+ 907.3296, obsd. 907.3296.

Workup

  1. customafter HPLC purification

Sources & evidence

ORD record
ord-0fa5a9dff56f4fc9907f4f350502c438
Source dataset
uspto-grants-2016_09
Patent number
US09447035B2

Reaction notes

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