Acetyl chloride → HCID 58710695, compound

HRID 1442988Notes

Reaction equation

HRID 1442988 reaction equation
C(N(CC)C(C)C)(C)C.[C:10](Cl)(=[O:12])[CH3:11].[Cl:14][C:15]1[CH:16]=[C:17]([NH:22][C:23]2[C:32]3[C:27](=[CH:28][C:29]([O:40][CH3:41])=[CH:30][C:31]=3[O:33][CH2:34][C@H:35]3[CH2:39][CH2:38][CH2:37][NH:36]3)[N:26]=[CH:25][N:24]=2)[CH:18]=[CH:19][C:20]=1[F:21]>C(Cl)Cl>[C:10]([N:36]1[CH2:37][CH2:38][CH2:39][C@@H:35]1[CH2:34][O:33][C:31]1[CH:30]=[C:29]([O:40][CH3:41])[CH:28]=[C:27]2[C:32]=1[C:23]([NH:22][C:17]1[CH:18]=[CH:19][C:20]([F:21])=[C:15]([Cl:14])[CH:16]=1)=[N:24][CH:25]=[N:26]2)(=[O:12])[CH3:11]

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 68676941HCID 68676941, compound

Product 1

HCID 58710695HCID 58710695, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

N,N-Diisopropylethylamine (52 μl) and acetyl chloride (21 μl) were added sequentially, each in one portion, to a stirred mixture of N-(3-chloro-4-fluorophenyl)-7-methoxy-5-[(2R)-pyrrolidin-2-ylmethoxy]-quinazolin-4-amine (100 mg) in DCM (2 ml) at room temperature. The reaction mixture was stirred for 1 hour and then diluted with DCM (10 ml) and washed with saturated aqueous sodium hydrogen carbonate. The organic layer was dried (MgSO4) and concentrated in vacuo to leave a yellow solid, which was purified by column chromatography using 24% methanol in DCM as eluent, followed by trituration with ether to give the title compound as a white solid (92 mg, 83%); NMR Spectrum (DMSO-d6) 9.90 (br s, 1H), 8.40 (s, 1H), 8.15 (m, 1H), 7.65 (m, 1H), 7.40 (m, 1H), 6.80 (m, 2H), 4.60 (m, 1H), 4.50 (m, 1H), 4.25 (m, 1H), 3.95 (s, 3H), 3.50 (m, 1H), 3.30 (s, 3H), 2.0-1.85 (m, 5H); Mass spectrum MH+ 445.

Workup

  1. washwashed with saturated aqueous sodium hydrogen carbonate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. customto leave a yellow solid, which
  5. customwas purified by column chromatography

Sources & evidence

ORD record
ord-d60d41b9d40e40a0a8588e0c7db57779
Source dataset
uspto-grants-2010_02
Patent number
US07659279B2

Reaction notes

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