Acetonitrile → HCID 57562999, compound

HRID 1726276Notes

Reaction equation

HRID 1726276 reaction equation
[F:1][C:2]([F:33])([F:32])[O:3][C:4]1[CH:9]=[CH:8][C:7]([NH:10][CH:11]2[CH2:16][CH2:15][N:14]([C@H:17]([CH3:31])[CH2:18][CH2:19][NH:20][C:21]([C:23]3[C:28]([CH3:29])=[N:27][CH2:26][N:25](C)[CH:24]=3)=[O:22])[CH2:13][CH2:12]2)=[CH:6][CH:5]=1.Br[CH2:35][C:36]1[CH:40]=[CH:39][S:38][CH:37]=1.[CH3:41]C#N>>[S:38]1[CH:39]=[CH:40][C:36]([CH2:35][N:10]([C:7]2[CH:6]=[CH:5][C:4]([O:3][C:2]([F:32])([F:33])[F:1])=[CH:9][CH:8]=2)[CH:11]2[CH2:16][CH2:15][N:14]([C@H:17]([CH3:31])[CH2:18][CH2:19][NH:20][C:21]([C:23]3[C:28]([CH3:29])=[N:27][CH:26]=[N:25][C:24]=3[CH3:41])=[O:22])[CH2:13][CH2:12]2)=[CH:37]1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 5207033-(Bromomethyl)thiopheneHCID 131727287HCID 131727287, compound

Product 1

HCID 57562999HCID 57562999, compoundYield 10%

Procedure

A solution of the above amide (123 mg, 0.26 mmol) and 3-(bromomethyl)thiophene (56 mg, 0.32 mmol) in CH3CN (3 mL) was stirred overnight. Standard work-up and purification afforded COMPOUND 291 as a white foam (15 mg, 10%). 1H NMR (CDCl3) δ 1.01 (d, 3H, J=9.0 Hz), 1.77 (d, 4H, J=9.0 Hz), 2.16 (t, 1H, J=12.0 Hz), 2.52 (s, 6H), 2.59 (d, 1H, J=9.0 Hz), 2.73-2.78 (m, 1H), 2.83-2.90 (m, 2H), 3.33 (td, 1H, J=9.0, 3.0 Hz), 3.55 (td, 1H, J=9.0, 3.0 Hz), 3.84 (s, 2H), 3.86-3.91 (m, 1H), 6.57 (d, 2H, J=9.0 Hz), 6.96-7.02 (m, 4H), 7.30 (dd, 1H, J=6.0, 3.0 Hz), 8.71 (d, 1H, J=3.0 Hz), 8.88 (s, 1H). ES-MS m/z 562 [M+H]+.

Workup

  1. customStandard work-up and purification

Sources & evidence

ORD record
ord-2ec90baf0ff84645a650b5892d1a787f
Source dataset
uspto-grants-2009_02
Patent number
US07491735B2

Reaction notes

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