Diisopropylethylamine → HCID 178482836, compound

HRID 1844988Notes

Reaction equation

HRID 1844988 reaction equation
N1C=CN=[C:2]1[NH:6][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.CCN(C(C)C)C(C)C.[F:64][C:65]1[CH:73]=[CH:72][C:68]([CH2:69]NC)=[CH:67][CH:66]=1>CN(C=O)C>[F:64][C:65]1[CH:73]=[CH:72][C:68]([CH2:69][N:6]([CH3:2])[C:7]([C:9]2[C:17]3[NH: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])=[N:14][C:13]=3[CH:12]=[CH:11][CH:10]=2)=[O:8])=[CH:67][CH:66]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 7368601-(4-fluorophenyl)-N-methylmethanamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 58026665HCID 58026665, compound

Product 1

HCID 178482836HCID 178482836, compoundYield 66.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 100 mg (0.3 mmol) of 2-[(isoquinoline-3-carbonyl)-amino]-3H-benzoimidazole-4-carboxylic acid (from Example 58) in DMF (2 mL) was added 200 mg (0.53 mmol) of HBTU and DIEA (0.5 mL). The mixture was stirred for 5 min then 140 mg (1.0 mmol) of N-(4-fluoro-benzyl)-N-methyl-amine was added. The resulted reaction mixture was heated at 70° C. for 1 h. After usual workup as described in general procedure A, the residue was purified by column chromatography eluting with DCM/EtOAc (v/v=1:1) to afford the 90 mg (66%) of isoquinoline-3-carboxylic acid {7-[(4-fluoro-benzyl)-methyl-carbamoyl]-1H-benzoimidazol-2-yl}-amide. LCMS: 454 (M+1)+.

Workup

  1. customThe resulted reaction mixture
  2. customthe residue was purified by column chromatography
  3. washeluting with DCM/EtOAc (v/v=1:1)

Sources & evidence

ORD record
ord-0333402d60fa493498bce3980eea6348
Source dataset
uspto-grants-2015_02
Patent number
US08946259B2

Reaction notes

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