HCID 22182383, compound → HCID 21026551, compound

HRID 1432171Notes

Reaction equation

HRID 1432171 reaction equation
[CH2:1]([C:5]1[S:20][C:8]2[N:9]=[CH:10][N:11]=[C:12]([NH:13][CH:14]3[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]3)[C:7]=2[CH:6]=1)[CH:2]([CH3:4])[CH3:3].CS(O[CH:26]([C:28]1[CH:33]=[C:32]([F:34])[CH:31]=[C:30]([F:35])[CH:29]=1)[CH3:27])(=O)=O>>[F:34][C:32]1[CH:33]=[C:28]([CH:26]([N:17]2[CH2:18][CH2:19][CH:14]([NH:13][C:12]3[C:7]4[CH:6]=[C:5]([CH2:1][CH:2]([CH3:4])[CH3:3])[S:20][C:8]=4[N:9]=[CH:10][N:11]=3)[CH2:15][CH2:16]2)[CH3:27])[CH:29]=[C:30]([F:35])[CH:31]=1

Participants

3

Reactant 2

HCID 22182383HCID 22182383, compoundHCID 22182414HCID 22182414, compound

Product 1

HCID 21026551HCID 21026551, compound

Procedure

The title compound was prepared (127 mg, 69%) from 6-isobutyl-N-(piperidin-4-yl)thieno[2,3-d]pyrimidin-4-amine (125 mg, 0.43 mmol) and 1-(3,5-difluorophenyl)ethyl methanesulfonate (243 mg, 1.03 mmol) by following the general procedure described for Preparation 12. 1H NMR (400 MHz, CDCl3): δ 8.40 (s, 1H), 6.90 (m, 2H), 6.75 (s, 1H), 6.70 (m, 1H), 4.95 (d, 1H), 4.15 (m, 1H), 3.45 (m, 1H), 2.95 (m, 1H), 2.80 (m, 1H), 2.70 (d, 2H), 2.20 (m, 4H), 1.95 (m, 1H), 1.55 (m, 2H), 1.35 (d, 3H), 0.95 (d, 6H). MS (ESI) m/z: Calculated: 430.56; Observed: 431.1 (M++1).

Workup

  1. customdescribed for Preparation 12

Sources & evidence

ORD record
ord-915bd003e0884f14aa328701df92362c
Source dataset
uspto-grants-2009_11
Patent number
US07612078B2

Reaction notes

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