Acetic Acid → HCID 68750968, compound

HRID 1864783Notes

Reaction equation

C([BH3-])#N.[F:4][C:5]1[CH:55]=[CH:54][C:8]([C:9]([N:11]([CH2:18][C:19]2[CH:24]=[C:23]([C:25]3[CH:52]=[CH:51][C:28]4[N:29]([C:32]([C:45]5[CH:50]=[CH:49][CH:48]=[CH:47][CH:46]=5)([C:39]5[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=5)[C:33]5[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=5)[N:30]=[N:31][C:27]=4[CH:26]=3)[CH:22]=[CH:21][C:20]=2[F:53])[CH:12]2[CH2:17][CH2:16][NH:15][CH2:14][CH2:13]2)=[O:10])=[CH:7][CH:6]=1.C(O[C:59]1(O[Si](C)(C)C)[CH2:61][CH2:60]1)C.C(O)(=O)C>CO>[CH:59]1([N:15]2[CH2:16][CH2:17][CH:12]([N:11]([CH2:18][C:19]3[CH:24]=[C:23]([C:25]4[CH:52]=[CH:51][C:28]5[N:29]([C:32]([C:39]6[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=6)([C:45]6[CH:46]=[CH:47][CH:48]=[CH:49][CH:50]=6)[C:33]6[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=6)[N:30]=[N:31][C:27]=5[CH:26]=4)[CH:22]=[CH:21][C:20]=3[F:53])[C:9](=[O:10])[C:8]3[CH:7]=[CH:6][C:5]([F:4])=[CH:55][CH:54]=3)[CH2:13][CH2:14]2)[CH2:61][CH2:60]1

Participants

Conditions

Temperature: 45 °C

Procedure

Solid supported cyanoborohydride (2.5 mmol/g, 46 mg) was added to a solution of 4-fluoro-N-[2-fluoro-5-(1-trityl-1H-benzotriazol-5-yl)-benzyl]-N-piperidin-4-yl-benzamide (20 mg, 0.029 mmol), (1-ethoxy-cyclopropoxy)-trimethylsilane (25 mg, 0.145 mmol) and acetic acid (1.74 mg, 0.029 mmol) in 1 mL of methanol. The mixture was stirred at 45° C. for 2 h and then at 75° C. overnight. The mixture was cooled and filtered and the filtrate concentrated in vacuo to provide the crude product. Chromatography provided 14 mg of product. LC/MS: Retention time, 3.20 min; (M+H)=730.

Workup

customat 75° C.
customovernight
temperatureThe mixture was cooled
filtrationfiltered
concentrationthe filtrate concentrated in vacuo
customto provide the crude product

Sources & evidence

ORD record: ord-36ba7011e17e4969958dc0a72a5c1496
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07625889B2

Reaction notes

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