tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamate → N-(tert-butoxycarbonyl)-N'-[(5-isoquinolyl)sulfonyl]-1,3-xylylenediamine

HRID 10602Notes

Reaction equation

HRID 10602 reaction equation
Cl.[CH:2]1[C:11]2[CH:10]=[CH:9][CH:8]=[C:7]([S:12](Cl)(=[O:14])=[O:13])[C:6]=2[CH:5]=[CH:4][N:3]=1.[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]1[CH:26]=[C:27]([CH:30]=[CH:31][CH:32]=1)[CH2:28][NH2:29])=[O:22])([CH3:19])([CH3:18])[CH3:17]>>[C:16]([O:20][C:21]([NH:23][CH2:24][C:25]1[CH:32]=[CH:31][CH:30]=[C:27]([CH2:28][NH:29][S:12]([C:7]2[CH:8]=[CH:9][CH:10]=[C:11]3[C:6]=2[CH:5]=[CH:4][N:3]=[CH:2]3)(=[O:14])=[O:13])[CH:26]=1)=[O:22])([CH3:19])([CH3:17])[CH3:18]

Participants

3

Reactant 2

HCID 2756043tert-butyl N-((3-(aminomethyl)phenyl)methyl)carbamateHCID 13116932Isoquinoline-5-sulfonyl chloride hydrochloride

Product 1

HCID 69525002N-(tert-butoxycarbonyl)-N'-[(5-isoquinolyl)sulfonyl]-1,3-xylylenediamineYield 78.1%

Procedure

According to Reference Example 5, Step B, a reaction was performed by using isoquinoline-5-sulfonyl chloride hydrochloride (9 g) and Intermediate 62 (8 g) to obtain the title compound (11.3 g).

Sources & evidence

ORD record
ord-5c0b777ddedc4173bf1e910f3e6f9fd8
Source dataset
uspto-grants-2006_08
Patent number
US07094789B2

Reaction notes

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