2-Methoxyethylamine → HCID 68097233, compound

HRID 625375Notes

Reaction equation

HRID 625375 reaction equation
[CH3:1][N:2]([CH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:64])[NH:31][C:32]2[CH:37]=[CH:36][C:35]([N:38]3[CH2:43][CH2:42][CH2:41][CH2:40][CH2:39]3)=[CH:34][C:33]=2[C:44]2[CH:49]=[C:48]([C:50](=[O:63])[NH:51][CH2:52][C:53]3[CH:58]=[CH:57][CH:56]=[C:55]([C:59]([F:62])([F:61])[F:60])[CH:54]=3)[CH:47]=[CH:46][N:45]=2)[N:25]=1)[CH2:3][CH2:4][N:5]1[CH2:10][CH2:9][N:8]([C:11](OC2C=CC([N+]([O-])=O)=CC=2)=[O:12])[CH2:7][CH2:6]1.[CH3:65][O:66][CH2:67][CH2:68][NH2:69].C(N(CC)C(C)C)(C)C>CN(C)C=O>[CH3:65][O:66][CH2:67][CH2:68][NH:69][C:11]([N:8]1[CH2:7][CH2:6][N:5]([CH2:4][CH2:3][N:2]([CH3:1])[CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30](=[O:64])[NH:31][C:32]3[CH:37]=[CH:36][C:35]([N:38]4[CH2:39][CH2:40][CH2:41][CH2:42][CH2:43]4)=[CH:34][C:33]=3[C:44]3[CH:49]=[C:48]([C:50](=[O:63])[NH:51][CH2:52][C:53]4[CH:58]=[CH:57][CH:56]=[C:55]([C:59]([F:60])([F:62])[F:61])[CH:54]=4)[CH:47]=[CH:46][N:45]=3)[N:25]=2)[CH2:10][CH2:9]1)=[O:12]

Participants

5

Reactant 3

HCID 80182-MethoxyethylamineHCID 81531DiisopropylethylamineHCID 66586793HCID 66586793, compound

Product 1

HCID 68097233HCID 68097233, compoundYield 25.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 4-nitrophenyl 4-(2-(methyl((6-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenylcarbamoyl)pyridin-2-yl)methyl)-amino)ethyl)piperazine-1-carboxylate (100 mg, 0.11 mmol, 1.00 equiv) in N,N-dimethylformamide (5 mL), 2-methoxyethanamine (10 mg, 0.13 mmol, 1.00 equiv), and N,N-diisopropylethylamine (45 mg, 0.35 mmol, 3.00 equiv). The resulting solution was stirred overnight at room temperature. The mixture was concentrated under vacuum. The crude product (0.1 g) was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA. The product was obtained as 23.2 mg (18%) of a yellow solid. 1H-NMR (300 MHz, DMSO-d6, ppm): δ 12.76 (s, 1H), 9.54-9.52 (m, 1H), 9.05-9.03 (m, 1H), 8.48-8.45 (m, 1H), 8.26 (m, 1H), 8.14-8.12 (m, 2H), 7.88-7.86 (m, 1H), 7.79-7.24 (m, 7H), 6.71 (m, 1H), 4.65-4.63 (d, J=5.7 Hz, 2H), 4.09 (m, 3H), 3.69-3.01 (m, 23H), 1.71-1.59 (m, 6H). MS (ES, m/z): 816 [M+H]+.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe mixture was concentrated under vacuum
  3. customThe crude product (0.1 g) was purified by reverse phase HPLC
  4. washeluting with a water/CH3CN gradient
  5. additioncontaining 0.05% TFA

Sources & evidence

ORD record
ord-24519a3bf4cc400bb79e6a2a8fc5da8a
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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