Acetyl chloride → HCID 66588081, compound

HRID 625371Notes

Reaction equation

HRID 625371 reaction equation
[N:1]1([CH2:8][C:9]2[N:14]=[C:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]4)=[CH:20][C:19]=3[C:30]3[CH:35]=[C:34]([C:36](=[O:49])[NH:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:48])([F:47])[F:46])[CH:40]=4)[CH:33]=[CH:32][N:31]=3)=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH2:7][CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.[C:57](Cl)(=[O:59])[CH3:58]>ClCCl>[C:57]([N:4]1[CH2:5][CH2:6][CH2:7][N:1]([CH2:8][C:9]2[N:14]=[C:13]([C:15]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([N:24]4[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]4)=[CH:20][C:19]=3[C:30]3[CH:35]=[C:34]([C:36](=[O:49])[NH:37][CH2:38][C:39]4[CH:44]=[CH:43][CH:42]=[C:41]([C:45]([F:47])([F:46])[F:48])[CH:40]=4)[CH:33]=[CH:32][N:31]=3)=[O:16])[CH:12]=[CH:11][CH:10]=2)[CH2:2][CH2:3]1)(=[O:59])[CH3:58]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 66587534HCID 66587534, compound

Product 1

HCID 66588081HCID 66588081, compoundYield 88.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Into a 50-mL round-bottom flask, was placed a solution of 6-((1,4-diazepan-1-yl)methyl)-N-(4-(piperidin-1-yl)-2-(4-(3-(trifluoromethyl)benzylcarbamoyl)pyridin-2-yl)phenyl)picolinamide (135 mg, 0.19 mmol, 1.00 equiv, 95%) in dichloromethane (5 mL), triethylamine (40 mg, 0.39 mmol, 2.00 equiv, 99%), and acetyl chloride (18 mg, 0.23 mmol, 1.20 equiv, 99%). The resulting solution was stirred for 3 h at room temperature. The resulting solution was diluted with 50 mL of dichloromethane. The resulting mixture was washed with 1×50 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The resulting mixture was washed with 2×10 mL of hexane. The product was obtained as 120 mg (87%) of a yellow solid. 1H-NMR (400 MHz, DMSO-d6, ppm): δ 12.86 (s, 1H), 9.54-9.51 (t, 1H), 9.00 (s, 1H), 8.51-8.49 (d, J=6 Hz, 1H), 8.23 (s, 1H), 8.00 (s, 2H), 7.88-7.86 (d, 1H), 7.72-7.55 (m 5H), 7.33 (s, 1H), 7.14-7.11 (d, J=9 Hz, 1H), 4.63 (s, 2H), 3.91-3.88 (s, J=9 Hz, 2H), 3.52-3.50 (m, 4H), 3.21-3.19 (m, 4H), 2.78-2.63 (m, 4H), 2.01-1.98 (d, J=9 Hz, 3H), 1.79-1.55 (m, 8H). MS (ES, m/z): 714 [M+H]+.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. washThe resulting mixture was washed with 1×50 mL of brine
  3. dry with materialThe mixture was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under vacuum
  5. washThe resulting mixture was washed with 2×10 mL of hexane

Sources & evidence

ORD record
ord-18aa144b07f346c68c16658bbf3a46bb
Source dataset
uspto-grants-2016_04
Patent number
US09301951B2

Reaction notes

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