Triethylamine → (R)-N-(1-aminopropan-2-yl)isoquinoline-6-sulfonamide dihydrochloride

HRID 334004Notes

Reaction equation

HRID 334004 reaction equation
[NH2:1][C@H:2]([CH3:12])[CH2:3][NH:4]C(=O)OC(C)(C)C.[CH:13]1[C:22]2[C:17](=[CH:18][C:19]([S:23]([Cl:26])(=[O:25])=[O:24])=[CH:20][CH:21]=2)[CH:16]=[CH:15][N:14]=1.C(N(CC)CC)C>ClCCl>[ClH:26].[ClH:26].[NH2:4][CH2:3][C@H:2]([NH:1][S:23]([C:19]1[CH:18]=[C:17]2[C:22](=[CH:21][CH:20]=1)[CH:13]=[N:14][CH:15]=[CH:16]2)(=[O:25])=[O:24])[CH3:12]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 45072491tert-butyl N-((2R)-2-aminopropyl)carbamateHCID 55280287Isoquinoline-6-sulfonyl chloride

Product 1

HCID 86699367(R)-N-(1-aminopropan-2-yl)isoquinoline-6-sulfonamide dihydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-tert-butyl 2-aminopropylcarbamate (338 mg) synthesized according to the method described in PCT publication No. WO2010/006085 was condensed with isoquinoline-6-sulfonyl chloride prepared in Reference Example 1 in the presence of triethylamine (0.538 mL) in dichloromethane to obtain a crude product. Subsequently, 252 mg of the title compound was obtained as a white solid (38%) with reference to the methods of Steps 2 and 3 of Example 1.

Workup

  1. customto obtain a crude product

Sources & evidence

ORD record
ord-82af080a607041e49c75d07010f4d384
Source dataset
uspto-grants-2014_11
Patent number
US08883792B2

Reaction notes

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