Acetyl chloride → HCID 10195373, compound

HRID 916419Notes

Reaction equation

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

Participants

Reactant 2

HCID 6367Acetyl chloride

HCID 58960225HCID 58960225, compound

Product 1

HCID 10195373HCID 10195373, compoundYield 58%

Procedure

Using an analogous procedure to that described for the preparation of Example 11, 4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxy-7-[(2S)-pyrrolidin-2-ylmethoxy]quinazoline. (120 mg, 0.28 mmol) was reacted with acetyl chloride (24 μl, 0.34 mmol). The crude product was purified by column chromatography eluting with methanol/methylene chloride (2/98) to give 7-[(2S)-1-acetylpyrrolidin-2-ylmethoxy]-4-[(4-fluoro-2-methyl-1H-indol-5-yl)oxy]-6-methoxyquinazoline (76 mg, 58%).

Workup

customThe crude product was purified by column chromatography
washeluting with methanol/methylene chloride (2/98)

Sources & evidence

ORD record: ord-d073e17e5ef54df785bfa5f176624210
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07268230B2

Reaction notes

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