Hydrochloric Acid → {5-[(7-benzenesulfonyl-4-cyclopentyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)-hydroxy-methyl]-pyridin-2-yl}-(6-trifluoromethyl-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester

HRID 1775172Notes

Reaction equation

[C:1]1([S:7]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)[C:13]=3[C:12](I)=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Mg]Cl)(C)C.[C:30]([O:34][C:35](=[O:56])[N:36]([C:48]1[CH:53]=[CH:52][C:51]([CH:54]=[O:55])=[CH:50][N:49]=1)[CH2:37][C:38]1[CH:39]=[N:40][C:41]([C:44]([F:47])([F:46])[F:45])=[CH:42][CH:43]=1)([CH3:33])([CH3:32])[CH3:31].Cl>O1CCCC1>[C:30]([O:34][C:35](=[O:56])[N:36]([C:48]1[CH:53]=[CH:52][C:51]([CH:54]([C:12]2[C:13]3[C:18]([CH:19]4[CH2:23][CH2:22][CH2:21][CH2:20]4)=[N:17][CH:16]=[N:15][C:14]=3[N:10]([S:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)(=[O:9])=[O:8])[CH:11]=2)[OH:55])=[CH:50][N:49]=1)[CH2:37][C:38]1[CH:39]=[N:40][C:41]([C:44]([F:47])([F:45])[F:46])=[CH:42][CH:43]=1)([CH3:33])([CH3:31])[CH3:32]

Participants

Conditions

Temperature: 0 °C

Procedure

To 7-benzenesulfonyl-4-cyclopentyl-5-iodo-7H-pyrrolo[2,3-d]pyrimidine (50, 0.119 g, 0.262 mmol) in 1.8 mL of tetrahydrofuran at −20° C. under nitrogen, isopropylmagnesium chloride (0.144 mL, 2.0 M in tetrahydrofuran, 0.289 mmol) was added and the reaction stirred and allowed to warm to 0° C. over 1 hour. The reaction was cooled to −15° C. and (5-formyl-pyridin-2-yl)-(6-trifluoromethyl-pyridin-3-ylmethyl)-carbamic acid tert-butyl ester (51, 0.120 g, 0.315 mmol) in 0.53 mL of tetrahydrofuran was added. The reaction was poured into 0.1 N aqueous hydrochloric acid and extracted with ethyl acetate.

Workup

temperatureThe reaction was cooled to −15° C.
extractionextracted with ethyl acetate

Sources & evidence

ORD record: ord-1f8b2f033cfc4fc4902064bc0a419d24
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260437B2

Reaction notes

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