Hydrochloric Acid → HCID 73505861, compound

HRID 590890Notes

Reaction equation

HRID 590890 reaction equation
[NH2:1][C:2]1[C:6]2[C:7](Cl)=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[NH:4][N:3]=1.[CH3:24][O-:25].[Na+].Cl>CO>[NH2:1][C:2]1[C:6]2[C:7]([O:25][CH3:24])=[N:8][C:9]([NH:11][C:12]([NH:14][C@@H:15]([C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH3:16])=[O:13])=[CH:10][C:5]=2[NH:4][N:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10942334Sodium MethoxideHCID 73505860HCID 73505860, compound

Product 1

HCID 73505861HCID 73505861, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of (R)-1-(3-amino-4-chloro-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea (0.12 g, 0.36 mmol) in methanol (3.0 mL) was added sodium methoxide (0.78 mL, 3.62 mmol, 25% solution in MeOH) and stirred at 120° C. for 1 h in a microwave reactor. After confirming the completion of reaction by TLC, the reaction mixture was acidified with 1.5N HCl and concentrated under reduced pressure and crude product which was purified by preparative HPLC to afford (R)-1-(3-amino-4-methoxy-1H-pyrazolo[4,3-c]pyridin-6-yl)-3-(1-phenylethyl)urea. 1H NMR (ppm, 400 MHz, DMSO-d6): δ 11.48 (s, 1H), 8.76 (s, 1H), 7.94 (s, 1H), 7.35-7.33 (m, 4H), 7.26-7.21 (m, 1H), 6.86 (d, J=8.00 Hz, 1H), 5.12 (s, 2H), 4.88-4.85 (m, 1H), 3.87 (s, 3H), 1.41 (d, J=8.00 Hz, 3H), MS ES calc'd. for C16H18N6O2 [M+H]+ 327. Found 327.

Workup

  1. customthe completion of reaction by TLC
  2. concentrationconcentrated under reduced pressure and crude product which
  3. customwas purified by preparative HPLC

Sources & evidence

ORD record
ord-ad83353d6db3421a8dc2b3a8cf24fddf
Source dataset
uspto-grants-2016_01
Patent number
US09233979B2

Reaction notes

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