Ammonia → HCID 178525827, compound

HRID 343407Notes

Reaction equation

HRID 343407 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]2[CH:24]=[C:23]3[C:19]([C:20]([CH:25]4[CH2:30][CH2:29][N:28]([CH2:31][C:32]([O:34]C(C)(C)C)=[O:33])[CH2:27][CH2:26]4)=[N:21][NH:22]3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1)=O)(C)(C)C.N>Cl>[NH:8]1[CH2:13][CH2:12][CH:11](/[CH:14]=[CH:15]/[C:16]2[CH:24]=[C:23]3[C:19]([C:20]([CH:25]4[CH2:30][CH2:29][N:28]([CH2:31][C:32]([OH:34])=[O:33])[CH2:27][CH2:26]4)=[N:21][NH:22]3)=[CH:18][CH:17]=2)[CH2:10][CH2:9]1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 178451206HCID 178451206, compound

Product 1

HCID 178525827HCID 178525827, compoundYield 72.8%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

4-{2-[3-(1-tert-Butoxycarbonylmethyl-piperidin-4-yl)-1H-indazol-6-yl]-(E)-vinyl}-piperidine-1-carboxylic acid tert-butyl ester (54.0 g) was added portionwise (ca. 9 portions) over 0.75 h to a stirred solution of 5M hydrochloric acid (270 ml) at 20°-25°, and the mixture was stirred at 20°-23° for 18 h. 880 Ammonia (54 ml) was added dropwise with caution over 0.75 h, maintaining the temperature between 18°-26°. The resulting solution (pH 1-2) was filtered through 1 micron graded glass fibre filter paper and the filter washed through with water (54 ml). Further 880 ammonia (36.2 ml) was added dropwise over 0.5 h maintaining the temperature between 22°-26° (pH 9-9.5). The suspension was stirred at 22°-230° for 3 h, and the resulting precipitate filtered off, washed with water (2×148 ml) and dried in vacuo to give the title compound as a white solid (27.6 g).

Workup

  1. temperaturemaintaining the temperature between 18°-26°
  2. filtrationThe resulting solution (pH 1-2) was filtered through 1 micron
  3. washthe filter washed through with water (54 ml)
  4. additionFurther 880 ammonia (36.2 ml) was added dropwise over 0.5 h
  5. temperaturemaintaining the temperature between 22°-26° (pH 9-9.5)
  6. stirringThe suspension was stirred at 22°-230° for 3 h
  7. filtrationthe resulting precipitate filtered off
  8. washwashed with water (2×148 ml)
  9. customdried in vacuo

Sources & evidence

ORD record
ord-36e74b75815741ff908609036edc4873
Source dataset
uspto-grants-1999_01
Patent number
US05861414

Reaction notes

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