Acetic Acid → HCID 9955924, compound

HRID 1443006Notes

Reaction equation

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

Participants

Reactant 2

HCID 176Acetic Acid

HCID 68676927HCID 68676927, compound

Product 1

HCID 9955924HCID 9955924, compoundYield 59%

Procedure

The procedure described in Example 20 was repeated using (3S,5R)-5-[({4-[3-chloro-4-fluoroanilino]-7-methoxyquinazolin-5-yl}oxy)methyl]pyrrolidin-3-ol (120 mg) with acetic acid (18 μl) to give the title compound as a white solid in 59% yield; NMR spectrum (DMSO-d6) 9.95 (s, 1H), 8.46 (s, 1H), 8.16-8.14 (m, 1H), 7.73-7.70 (m, 1H), 7.46 (t, 1H), 6.85 (s, 1H), 6.84 (s, 1H), 5.10 (m, 1H), 4.67-4.63 (m, 1H), 4.47-4.38 (m, 2H), 4.26-4.21 (m, 1H), 3.94 (s, 3H), 3.59 (dd, 1H), 3.41 (dd, 1H), 2.11-2.05 (m, 2H), 2.00 (s, 3H); Mass spectrum MH+ 461.

Sources & evidence

ORD record: ord-e69e1a040adc4a1fafe5678e3591ecb0
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07659279B2

Reaction notes

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