Acetyl chloride → HCID 11179632, compound

HRID 1864212Notes

Reaction equation

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

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 69058477HCID 69058477, compound

Product 1

HCID 11179632HCID 11179632, compoundYield 38%

Procedure

The procedure described in Example 5 was repeated using N-[3-chloro-4-(pyridin-2-ylmethoxy)phenyl]-5-[2-(cyclopropylamino)ethoxy]quinazolin-4-amine and acetyl chloride to give the title compound in 38% yield; NMR spectrum (DMSO-d6) 0.76-0.82 (m, 4H), 2.06 (s, 3H), 2.76-2.83 (m, 1H), 3.87 (t, 2H), 4.42 (t, 2H), 5.31 (s, 2H), 7.19 (d, 1H), 7.26 (d, 1H), 7.32-7.40 (m, 2H), 7.56-7.61 (m, 2H), 7.70-7.75 (m, 1H), 7.86-7.92 (m, 1H), 7.94-7.96 (m, 1H), 8.45 (s, 1H), 8.60 (d, 1H), 9.76 (s, 1H); Mass spectrum MH+ 504.

Sources & evidence

ORD record: ord-2643a047fbf5438f88e2ca69dc0e6946
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625908B2

Reaction notes

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