5-Cyano-2-fluorobenzaldehyde → 3-((4-(6-Chlorothieno[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)methyl)-4-fluorobenzonitrile

HRID 1432177Notes

Reaction equation

HRID 1432177 reaction equation
[Cl:1][C:2]1[S:17][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[C:4]=2[CH:3]=1.[F:18][C:19]1[CH:26]=[CH:25][C:22]([C:23]#[N:24])=[CH:21][C:20]=1[CH:27]=O>>[Cl:1][C:2]1[S:17][C:5]2[N:6]=[CH:7][N:8]=[C:9]([NH:10][CH:11]3[CH2:12][CH2:13][N:14]([CH2:27][C:20]4[CH:21]=[C:22]([CH:25]=[CH:26][C:19]=4[F:18])[C:23]#[N:24])[CH2:15][CH2:16]3)[C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 109097255-Cyano-2-fluorobenzaldehydeHCID 579331476-chloro-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine

Product 1

HCID 116470293-((4-(6-Chlorothieno[2,3-d]pyrimidin-4-ylamino)piperidin-1-yl)methyl)-4-fluorobenzonitrile

Procedure

The title compound was prepared (119 mg, 45%) from 6-chloro-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine (150 mg, 0.56 mmol) and 4-fluoro-3-formylbenzonitrile (83 mg, 0.56 mmol) by following the general procedure described for Preparation 11. 1H NMR (400 MHz, CDCl3): δ 8.45 (s, 1H), 7.85 (m, 1H), 7.60 (m, 1H), 7.15 (t, 1H), 7.00 (s, 1H), 5.00 (d, 1H), 4.20 (m, 1H), 3.60 (s, 2H), 2.90 (m, 2H), 2.35 (m, 2H), 2.15 (m, 2H), 1.60 (m, 2H). MS (ESI) m/z: Calculated: 401.09; Observed: 402.1 (M++1).

Workup

  1. customdescribed for Preparation 11

Sources & evidence

ORD record
ord-fbf70f9805ca4a2cb9ef0f052aeef823
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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