Acetic Anhydride → HCID 53476280, compound

HRID 1253572Notes

Reaction equation

HRID 1253572 reaction equation
[CH:1]1([NH:4][C:5]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[CH:29]=[CH:28][C:27]([CH2:30][NH:31][CH2:32][CH2:33][O:34][CH3:35])=[CH:26][N:25]=5)[S:23][C:16]=34)=[C:10]([F:36])[C:9]=2[F:37])=[O:6])[CH2:3][CH2:2]1.CO.C(Cl)Cl.[C:43](OC(=O)C)(=[O:45])[CH3:44]>>[CH:1]1([NH:4][C:5](=[O:6])[NH:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][C:15]3[CH:20]=[CH:19][N:18]=[C:17]4[CH:21]=[C:22]([C:24]5[N:25]=[CH:26][C:27]([CH2:30][N:31]([CH2:32][CH2:33][O:34][CH3:35])[C:43](=[O:45])[CH3:44])=[CH:28][CH:29]=5)[S:23][C:16]=34)=[C:10]([F:36])[C:9]=2[F:37])[CH2:2][CH2:3]1

Participants

4

Reactant 3

HCID 7918Acetic AnhydrideHCID 21226129Dichloromethane methanolHCID 67444256HCID 67444256, compound

Product 1

HCID 53476280HCID 53476280, compoundYield 38%

Procedure

A suspension of compound 25 (100 mg, 0.156 mmol, TFA salt) in acetic anhydride (1 mL) was stirred at RT for 2 days. The reaction mixture was quenched by addition of methanol and water. The fine suspension was collected by filtration, rinsed successively with water, 1N NaOH, water, and air-dried. The crude product was purified by Biotage (SNAP 25 g cartridge; MeOH/DCM: 0/100 to 10/90 over 20 CV, then 10/90 over 5 CV) to afford the title compound 26 (34 mg, 0.06 mmol, 38% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): mixture of rotamers, 8.57-8.44 (m, 3H), 8.38 and 8.34 (2s, 1H), 8.30 and 8.24 (2d, J=8.2 Hz, 1H), 8.04 (bt, J=8.3 Hz, 1H), 7.82-7.75 (m, 1H), 7.32-7.25 (m, 1H), 6.87 (bd, J=2.7 Hz, 1H), 6.79-6.74 (m, 1H), 4.71 and 4.59 (2s, 2H), 3.54-3.40 (m, 4H), 3.24 and 3.21 (2s, 3H), 2.61-2.53 (m, 1H), 2.13 and 2.05 (2s, 3H), 0.73-0.58 (m, 2H), 0.50-0.36 (m, 2H). MS (m/z): 568.6 (M+H).

Workup

  1. customThe reaction mixture was quenched by addition of methanol and water
  2. filtrationThe fine suspension was collected by filtration
  3. washrinsed successively with water, 1N NaOH, water
  4. customair-dried
  5. customThe crude product was purified by Biotage (SNAP 25 g cartridge

Sources & evidence

ORD record
ord-142183897c4249738b4eadabf706c8de
Source dataset
uspto-grants-2013_06
Patent number
US08455484B2

Reaction notes

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