Acetyl chloride → HCID 117777787, compound

HRID 64148Notes

Reaction equation

HRID 64148 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:35]=[CH:34][C:9]3[N:10]([C:13]4[CH:14]=[C:15]([NH:27][S:28]([CH:31]5[CH2:33][CH2:32]5)(=[O:30])=[O:29])[CH:16]=[C:17]([C:19]5[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=5[F:26])[CH:18]=4)[CH:11]=[N:12][C:8]=3[CH:7]=2)[CH:3]=[N:2]1.[C:36](Cl)(=[O:38])[CH3:37]>C(Cl)Cl>[C:36]([N:1]1[CH:5]=[C:4]([C:6]2[CH:35]=[CH:34][C:9]3[N:10]([C:13]4[CH:14]=[C:15]([NH:27][S:28]([CH:31]5[CH2:32][CH2:33]5)(=[O:29])=[O:30])[CH:16]=[C:17]([C:19]5[CH:24]=[CH:23][C:22]([F:25])=[CH:21][C:20]=5[F:26])[CH:18]=4)[CH:11]=[N:12][C:8]=3[CH:7]=2)[CH:3]=[N:2]1)(=[O:38])[CH3:37]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 117777927HCID 117777927, compound

Product 1

HCID 117777787HCID 117777787, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of the compound of Example 203 (50 mg, 0.101 mmol) in DCM (1 ml) was added TEA (0.1 ml, 0.69 mmol, 6.9 eq.) followed by acetyl chloride (12 mg, 0.142 mmol, 1.4 eq.). The mixture was stirred for 2 h and quenched and extracted as in Example 1(d). The solvent was distilled off to afford the crude residue which was purified by preparative HPLC to yield the product in 74% yield (40 mg). H-NMR (300 MHz, DMSO-D6) δ=8.93 (bs, 1H), 8.72 (s, 1H), 8.50 (s, 1H), 8.24 (s, 1H), 7.83 (d, 1H), 7.76-7.70 (m, 2H), 7.58 (bs, 2H), 7.50-7.40 (m, 2H), 7.30-7.20 (m, 1H), 3.15 (s, 3H), 2.90-2.80 (m, 1H), 2.67 (s, 3H), 1.01 (d, 4H); LC-MS (ESI): Calculated mass: 533.55; Observed mass: 534.1 [M+H]+ (rt: 1.55 min).

Workup

  1. customquenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off

Sources & evidence

ORD record
ord-2731518f9e114af28f640c7521e1d6d6
Source dataset
uspto-grants-2016_09
Patent number
US09447091B2

Reaction notes

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