HCID 66609624, compound → HCID 56848632, compound

HRID 473147Notes

Reaction equation

[F:1][C:2]([F:25])([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=1)[C:3]1[N:12]=[C:11](S(C)=O)[C:10]2[C:5](=[CH:6][C:7]([C:16]#[N:17])=[CH:8][CH:9]=2)[N:4]=1.BrC1C=C2C(C(SC)=[N:32][C:33]([C:37](F)(F)[C:38]3[CH:43]=CC(F)=C[N:39]=3)=[N:34]2)=CC=1>>[F:1][C:2]([F:25])([C:18]1[CH:23]=[CH:22][C:21]([F:24])=[CH:20][N:19]=1)[C:3]1[N:12]=[C:11]([NH:32][C:33]2[CH:37]=[C:38]([CH3:43])[NH:39][N:34]=2)[C:10]2[C:5](=[CH:6][C:7]([C:16]#[N:17])=[CH:8][CH:9]=2)[N:4]=1

Participants

Reactant 2

HCID 66609624HCID 66609624, compound

HCID 66610749HCID 66610749, compound

Product 1

HCID 56848632HCID 56848632, compound

Procedure

2-(Difluoro(5-fluoropyridin-2-yl)methyl)-4-(5-methyl-1H-pyrazol-3-ylamino)quinazoline-7-carbonitrile was prepared as a white solid (12 mg, 10%) by following a procedure analogous to that described in Example 7 Step D, substituting 2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylsulfinyl)quinazoline-7-carbonitrile for the 7-bromo-2-(difluoro(5-fluoropyridin-2-yl)methyl)-4-(methylthio)quinazoline used in Example 7. 1H NMR (300 MHz, DMSO-d6) δ 12.23-12.30 (m, 1H), 11.06 (s, 1H), 8.86 (d, J=8.7 Hz, 1H), 8.67 (s, 1H), 8.42 (d, J=1.1 Hz, 1H), 7.97-8.05 (m, 3H), 5.99 (s, 1H), 2.18 (s, 3H); LC-MS (ESI) m/z 396 (M+H)+.

Sources & evidence

ORD record: ord-6355c02606f24692b2b0450d03738648
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08633207B2

Reaction notes

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