3-(Bromomethyl)thiophene → HCID 57563070, compound

HRID 1726294Notes

Reaction equation

[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([NH:11][CH:12]2[CH2:17][CH2:16][N:15]([C@H:18]([CH3:32])[CH2:19][CH2:20][NH:21][C:22]([C:24]3[C:25]([CH3:31])=[N:26][CH:27]=[N:28][C:29]=3[CH3:30])=[O:23])[CH2:14][CH2:13]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2].Br[CH2:34][C:35]1[CH:39]=[CH:38][S:37][CH:36]=1>>[C:1]([NH:4][C:5]1[N:10]=[CH:9][C:8]([N:11]([CH2:34][C:35]2[CH:39]=[CH:38][S:37][CH:36]=2)[CH:12]2[CH2:13][CH2:14][N:15]([C@H:18]([CH3:32])[CH2:19][CH2:20][NH:21][C:22]([C:24]3[C:25]([CH3:31])=[N:26][CH:27]=[N:28][C:29]=3[CH3:30])=[O:23])[CH2:16][CH2:17]2)=[CH:7][CH:6]=1)(=[O:3])[CH3:2]

Participants

Reactant 2

HCID 5207033-(Bromomethyl)thiophene

HCID 86602137HCID 86602137, compound

Product 1

HCID 57563070HCID 57563070, compoundYield 21%

Procedure

Using general procedure H, 4,6-dimethyl-pyrimidine-5-carboxylic acid {(R)-3-[4-(6-acetylamino-pyridin-3-ylamino)-piperidin-1-yl]-butyl}-amide (see EXAMPLE 246) (343 mg, 0.780 mmol) and 3-(bromomethyl)thiophene (207 mg) gave COMPOUND 328 as a yellow foam (86 mg, 21%). 1H NMR (CDCl3) δ 0.94-1.22 (m, 2H), 1.01 (d, 3H, J=6.6 Hz), 1.55 (m, 1H), 1.75 (m, 3H), 2.10 (s, 3H), 2.19 (m, 1H), 2.51 (s, 6H), 2.55 (m, 1H), 2.73-2.89 (m, 3H), 3.32 (m, 1H), 3.48 (m, 1H), 3.84 (s, 2H), 3.87 (m, 1H), 7.49 (m, 3H), 7.27 (m, 1H), 7.65 (d, 1H, J=3.0 Hz), 7.93 (d, 1H, J=9.3 Hz), 8.06 (s, 1H), 8.63 (m, 1H), 8.83 (s, 1H). 13C NMR (CDCl3) δ 13.82, 22.33, 24.81, 29.56, 30.68, 31.10, 40.51, 53.91, 45.47, 52.40, 56.77, 60.75, 114.94, 121.30, 123.84, 126.63, 126.71, 131.23, 133.74, 140.77, 142.05, 143.02, 158.01, 163.43, 166.72, 168.47. ES-MS m/z 536 (M+H). Anal. Calcd. for C28H37N7SO2.1.1CH2Cl2: C, 55.56; H, 6.28; N, 15.58; S, 5.10. Found: C, 55.76; H, 6.30; N, 15.63; S, 5.27.

Sources & evidence

ORD record: ord-a4f80b637d50435eba6d432c8ee019b2
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07491735B2

Reaction notes

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