Formic Acid → 4-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-ynyl sulfamate

HRID 417891Notes

Reaction equation

HRID 417891 reaction equation
C(O)=O.Cl[S:5]([N:8]=C=O)(=[O:7])=[O:6].[NH2:11][C:12]1[N:13]=[C:14]([Cl:37])[C:15]2[C:20]([C:21]#[C:22][CH2:23][CH2:24][OH:25])=[CH:19][N:18]([CH2:26][C:27]3[C:32]([CH3:33])=[C:31]([O:34][CH3:35])[C:30]([CH3:36])=[CH:29][N:28]=3)[C:16]=2[N:17]=1>CN(C)C(=O)C.C(Cl)Cl>[S:5](=[O:6])(=[O:7])([O:25][CH2:24][CH2:23][C:22]#[C:21][C:20]1[C:15]2[C:14]([Cl:37])=[N:13][C:12]([NH2:11])=[N:17][C:16]=2[N:18]([CH2:26][C:27]2[C:32]([CH3:33])=[C:31]([O:34][CH3:35])[C:30]([CH3:36])=[CH:29][N:28]=2)[CH:19]=1)[NH2:8]

Participants

7

Reactant 3

HCID 284Formic AcidHCID 70918Chlorosulfonyl isocyanateHCID 119505104-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol

Product 1

HCID 577138644-(2-amino-4-chloro-7-((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl)but-3-ynyl sulfamate

Reagents, catalysts & solvents 3

HCID 31374DimethylacetamideCatalystHCID 6344DichloromethaneSolventHCID 31374DimethylacetamideSolvent

Procedure

A mixture of formic acid (0.463 g) and N,N-dimethylacetamide (1 drop) was added to a solution of chlorosulfonyl isocyanate (1.31 g) in DCM (9 mL), and heated to reflux for 3 h. The resulting solution was added to a solution of 4-[2-Amino-4-chloro-7-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]-but-3-yn-1-ol (see example 2) (200 mg) in DMA (10 mL) and stirred at rt for 30 min. Work-up and reverse-phase preparative HPLC gave the title compound, as a solid. HPLC Rt=4.96 min.

Workup

  1. temperatureheated
  2. temperatureto reflux for 3 h

Sources & evidence

ORD record
ord-9e95050e76b04f0b9605a03b584eba05
Source dataset
uspto-grants-2012_01
Patent number
US08093229B2

Reaction notes

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