Diisopropylethylamine → Methyl 8-methoxyisoquinoline-3-carboxylate

HRID 1910163Notes

Reaction equation

HRID 1910163 reaction equation
CO[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[CH:9]=[N:8][C:7]([C:13]([OH:15])=[O:14])=[CH:6]2.N1C=CN=C1N[C:22](C1C2NC(N)=NC=2C=CC=1)=[O:23].[CH3:34]N(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:34][O:15][C:13]([C:7]1[N:8]=[CH:9][C:10]2[C:5]([CH:6]=1)=[CH:4][CH:3]=[CH:12][C:11]=2[O:23][CH3:22])=[O:14]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 573069496-Methoxyisoquinoline-3-carboxylic acidHCID 178508178HCID 178508178, compound

Product 1

HCID 66940406Methyl 8-methoxyisoquinoline-3-carboxylateYield 97.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

224 mg (1.1 mmol) of 6-methoxy-isoquinoline-3-carboxylic acid was reacted with 242 mg (1 mmol) of intermediate B (2-amino-3H-benzoimidazole-4-carboxylic acid (1H-imidazol-2-yl)-amide), 569 mg (1.5 mmol) of HBTU, 0.704 ml (4 mmol) of DIEA and 5 mL of DMF stirring at 80° C. for 2 h as describe in general procedure A to provide 212.4 mg (50%) of the title compound. 1H-NMR (400 MHz, DMSO): 9.37(s, 1H), 8.71 (s, 1H), 8.24(d, 1H), 7.94(d, 1H), 7.82(d, 1H), 7.73(d, 1H), 7.49(dd, 1H), 7.34(t, 1H), 6.88(s, 1H), 6.76(s, 1H), 3.98 (s, 3H) ppm; LCMS: 428 (M+1)+.

Sources & evidence

ORD record
ord-d720657ac7ab4be89899fbcc4e249c51
Source dataset
uspto-grants-2013_12
Patent number
US08598353B2

Reaction notes

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