4-Methylsulfonylbenzylamine → HCID 58724523, compound

HRID 1844978Notes

Reaction equation

HRID 1844978 reaction equation
N1C=CN=C1N[C:7]([C:9]1[C:17]2[N:16]=[C:15]([NH:18][C:19]([C:21]3[N:22]=[CH:23][C:24]4[C:29]([CH:30]=3)=[CH:28][CH:27]=[CH:26][CH:25]=4)=[O:20])[NH:14][C:13]=2[CH:12]=[CH:11][CH:10]=1)=[O:8].CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[CH3:55][S:56]([C:59]1[CH:66]=[CH:65][C:62]([CH2:63][NH2:64])=[CH:61][CH:60]=1)(=[O:58])=[O:57]>CN(C=O)C.CCN(C(C)C)C(C)C>[CH3:55][S:56]([C:59]1[CH:66]=[CH:65][C:62]([CH2:63][NH:64][C:7]([C:9]2[C:17]3[N:16]=[C:15]([NH:18][C:19]([C:21]4[N:22]=[CH:23][C:24]5[C:29]([CH:30]=4)=[CH:28][CH:27]=[CH:26][CH:25]=5)=[O:20])[NH:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:61][CH:60]=1)(=[O:57])=[O:58]

Participants

6

Reactant 3

HCID 574214-MethylsulfonylbenzylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58026665HCID 58026665, compound

Product 1

HCID 58724523HCID 58724523, compoundYield 33.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 81531DiisopropylethylamineSolvent

Procedure

100 mg (0.3 mmol) of 2-[(isoquinoline-3-carbonyl)-amino]-1H-benzoimidazole-4-carboxylic acid (from Example 58) was reacted with 130 mg (0.33 mmol) of HBTU and 55 mg (0.3 mmol) 4-methanesulfonyl-benzylamine in 3.0 mL of DMF and 1.0 mL of DIEA as described in general procedure A. After the usual work up as described in general procedure A, 50 mg (33%) of isoquinoline-3-carboxylic acid [4-(4-methanesulfonyl-benzylcarbamoyl)-1H-benzoimidazol-2-yl]-amide was isolated. LCMS: 500 (M+1)+.

Sources & evidence

ORD record
ord-f283809eef5947bb9afaf155a6c197e6
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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