1-Pyrrolidinecarbonyl chloride → HCID 178455387, compound

HRID 715582Notes

Reaction equation

[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:40]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:21]4=[N:22][C:23]([C:27]5[CH:32]=[CH:31][C:30]([C@@H:33]6[CH2:38][CH2:37][C@H:36]([OH:39])[CH2:35][CH2:34]6)=[CH:29][CH:28]=5)=[C:24]([Cl:26])[CH:25]=[C:20]4[N:19]=3)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N:49]1([C:54](Cl)=[O:55])[CH2:53][CH2:52][CH2:51][CH2:50]1>N1C=CC=CC=1>[N:49]1([C:54]([O:39][C@H:36]2[CH2:37][CH2:38][C@@H:33]([C:30]3[CH:31]=[CH:32][C:27]([C:23]4[N:22]=[C:21]5[N:40]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:18]([O:17][C@@H:16]6[CH2:15][O:14][C@@H:13]7[C@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])[CH2:10][O:11][C@H:12]67)=[N:19][C:20]5=[CH:25][C:24]=4[Cl:26])=[CH:28][CH:29]=3)[CH2:34][CH2:35]2)=[O:55])[CH2:53][CH2:52][CH2:51][CH2:50]1

Participants

Conditions

Temperature: 70 °C

Procedure

(cis)-4-(4-(2-((3R,3aR,6R,6aS)-6-(tert-Butyldimethylsilyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-5-yl)phenyl)cyclohexanol (50 mg) is dissolved in pyridine (1 mL), treated with pyrrolidine-1-carbonyl chloride (80 μL) and stirred for 12 hours at 70° C. Pyrrolidine-1-carbonyl chloride (160 μL) is added and the mixture is stirred for 48 hours at 100° C.

Workup

stirringthe mixture is stirred for 48 hours at 100° C.

Sources & evidence

ORD record: ord-3dc6df915ea44279871bdc73f1a94a54
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09187477B2

Reaction notes

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