Chlorosulfamic acid → HCID 86614252, compound

HRID 222177Notes

Reaction equation

[Si:1]([O:8][C@H:9]1[CH2:13][C@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][CH2:24][CH:25]4[CH2:27][CH2:26]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:11][C@H:10]1[CH2:28][OH:29])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl[S:31]([NH2:34])(=[O:33])=[O:32]>C(C#N)(C)=O>[S:31](=[O:33])(=[O:32])([O:29][CH2:28][C@@H:10]1[CH2:11][C@@H:12]([N:14]2[C:18]3[N:19]=[CH:20][N:21]=[C:22]([NH:23][CH2:24][CH:25]4[CH2:27][CH2:26]4)[C:17]=3[CH:16]=[CH:15]2)[CH2:13][C@@H:9]1[O:8][Si:1]([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2])[NH2:34]

Participants

Conditions

Temperature: 0 °C

Procedure

((1S,2S,4R)-2-{[tert-Butyl(dimethyl)silyl]oxy}-4-{4-[(cyclopropylmethyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl)methanol (74.0 mg, 0.178 mmol) was dissolved in AcCN (3.50 mL) and cooled to 0° C. TEA (0.0500 mL, 0.355 mmol) was added followed by a 2.00 M solution of chlorosulfonamide in AcCN (0.178 mL, 0.356 mmol, as prepared in 1j). The reaction was stirred for 2 h, quenched with MeOH and concentrated in vacuo. The material was taken on to the next step without further purification. LC/MS: Rt=1.51 min, ES+ 496 (FA standard).

Workup

customquenched with MeOH
concentrationconcentrated in vacuo
customThe material was taken on to the next step without further purification

Sources & evidence

ORD record: ord-2351e5bedee24ddf8b5091db76fd4e9a
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08207177B2

Reaction notes

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