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Chlorosulfamic acid → (1S,2S,4R)-2-{[(Aminosulfonyl)oxy]methyl}-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl acetate

HRID 222153
Notes
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Reaction equation

HRID 222153 reaction equation
[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([NH:19][C@@H:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:22][CH2:21]4)[C:13]=3[CH:12]=[CH:11]2)[CH2:7][C@H:6]1[CH2:29][OH:30])(=[O:3])[CH3:2].Cl[S:32]([NH2:35])(=[O:34])=[O:33]>C(C#N)(C)=O>[C:1]([O:4][C@H:5]1[CH2:9][C@H:8]([N:10]2[C:14]3[N:15]=[CH:16][N:17]=[C:18]([NH:19][C@@H:20]4[C:28]5[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=5)[CH2:22][CH2:21]4)[C:13]=3[CH:12]=[CH:11]2)[CH2:7][C@H:6]1[CH2:29][O:30][S:32]([NH2:35])(=[O:34])=[O:33])(=[O:3])[CH3:2]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 24499Chlorosulfamic acid2×HCID 66618460(1S,2S,4R)-4-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentyl acetate

Product 1

HCID 86614245(1S,2S,4R)-2-{[(Aminosulfonyl)oxy]methyl}-4-{4-[(1S)-2,3-dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]pyrimidin-7-yl}cyclopentyl acetateYield 94%

Reagents, catalysts & solvents 1

HCID 69430
2-Oxopropiononitrile
Solvent
3×

Conditions

Temperature
0 °C

Procedure

(1S,2S,4R)-4-{4-[(1S)-2,3-Dihydro-1H-inden-1-ylamino]-7H-pyrrolo[2,3-d]-pyrimidin-7-yl}-2-(hydroxymethyl)cyclopentyl acetate (2.30 g, 5.38 mol) was dissolved in AcCN (108 mL) and TEA (3.75 mL, 26.9 mmol) was added. The solution was cooled to 0° C. and a 2.00 M solution of chlorosulfonamide in AcCN (5.38 mL, 10.8 mmol, as prepared above) was added. The mixture was stirred at rt for 45 min. TLC indicated 50% conversion. Additional 2.00 M chlorosulfonamide in AcCN solution (5.38 mL, 10.8 mmol) was added and the mixture was stirred at rt for 15 min. At this time, TLC indicated complete conversion. The mixture was quenched with MeOH (3.00 mL), and the solvent was removed in vacuo. The residue was purified via silica gel chromatography eluting with a gradient of 0 to 10% MeOH in EtOAc to afford the title compound (2.45 g, 94%). LC/MS: Rt=1.68 min, ES+ 486 (AA standard).

Workup

  1. stirringthe mixture was stirred at rt for 15 min
  2. customThe mixture was quenched with MeOH (3.00 mL)
  3. customthe solvent was removed in vacuo
  4. customThe residue was purified via silica gel chromatography
  5. washeluting with a gradient of 0 to 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-86086432ff3e445c9dfbff5ecaf6880f
Source dataset
uspto-grants-2012_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08207177B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes