Triethylamine → HCID 56601991, compound

HRID 2406074Notes

Reaction equation

HRID 2406074 reaction equation
Br[CH2:2][C:3]1[CH:4]=[C:5]([CH:36]=[CH:37][CH:38]=1)[C:6]([NH:8][C:9]1[CH:29]=[CH:28][C:27]([N:30]2[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]2)=[CH:26][C:10]=1[C:11]([NH:13][C:14]1[CH:15]=[N:16][C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:18][CH:19]=1)=[O:12])=[O:7].[SH:39][C:40]1[CH:41]=[C:42]([CH:46]=[CH:47][CH:48]=1)[C:43]([OH:45])=[O:44].C(N(CC)CC)C>CN(C)C=O.O>[C:20]1([C:17]2[N:18]=[CH:19][C:14]([NH:13][C:11]([C:10]3[CH:26]=[C:27]([N:30]4[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]4)[CH:28]=[CH:29][C:9]=3[NH:8][C:6]([C:5]3[CH:4]=[C:3]([CH:38]=[CH:37][CH:36]=3)[CH2:2][S:39][C:40]3[CH:41]=[C:42]([CH:46]=[CH:47][CH:48]=3)[C:43]([OH:45])=[O:44])=[O:7])=[O:12])=[CH:15][N:16]=2)[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 95737Benzoic acid, 3-mercapto-HCID 66586921HCID 66586921, compound

Product 1

HCID 56601991HCID 56601991, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-(3-(bromomethyl)benzamido)-N-(2-phenylpyrimidin-5-yl)-5-(piperidin-1-yl)benzamide (120 mg, 0.23 mmol, 1.00 equiv) in N,N-dimethylformamide (10 mL) was added 3-mercaptobenzoic acid (42.12 mg, 0.27 mmol, 1.20 equiv) and triethylamine (46.08 mg, 0.46 mmol, 2.00 equiv) and the resulting solution was stirred for 3 h at room temperature. The mixture was diluted with 70 mL of water, extracted with 3×50 mL of ethyl acetate and the organic layers combined, dried over sodium sulfate, and concentrated under vacuum. The crude product (100 mg) was purified by reverse phase HPLC eluting with a water/CH3CN gradient containing 0.05% TFA to afford 24.7 mg (17%) of a light yellow solid. 1H-NMR (300 MHz, DMSO, ppm): δ 10.94 (m, 2H), 9.23 (d, J=9.3 Hz, 2H), 8.36 (m, 2H), 8.12 (d, J=9 Hz, 1H), 7.95 (s, 1H), 7.85 (s, 1H), 7.73 (m, 2H), 7.45 (m, 9H) 4.39 (s, 2H), 3.33 (s, 4H), 1.72 (s, 6H). MS (ES, m/z): 644 [M+H]+.

Workup

  1. extractionextracted with 3×50 mL of ethyl acetate
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated under vacuum
  4. customThe crude product (100 mg) was purified by reverse phase HPLC
  5. washeluting with a water/CH3CN gradient
  6. additioncontaining 0.05% TFA

Sources & evidence

ORD record
ord-4780ebf2bb86481d92571ceb38098d15
Source dataset
uspto-grants-2014_08
Patent number
US08809339B2

Reaction notes

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