Hydrochloric Acid → 4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride

HRID 2093918Notes

Reaction equation

HRID 2093918 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:21]3[N:22]=[CH:23][N:24]=[C:25]([C:26]4[C:34]5[O:33][CH2:32][O:31][C:30]=5[CH:29]=[CH:28][C:27]=4[O:35][CH2:36][CH:37]4[CH2:39][CH2:38]4)[C:20]=3[NH:19][CH:18]=2)=[O:16])[CH2:10][CH2:9]1)=O)(C)(C)C.CC(O)C.[ClH:44].C(OC)(C)(C)C>O1CCOCC1>[ClH:44].[NH:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15]([C:17]2[C:21]3[N:22]=[CH:23][N:24]=[C:25]([C:26]4[C:34]5[O:33][CH2:32][O:31][C:30]=5[CH:29]=[CH:28][C:27]=4[O:35][CH2:36][CH:37]4[CH2:38][CH2:39]4)[C:20]=3[NH:19][CH:18]=2)=[O:16])[CH2:10][CH2:9]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3776IsopropanolHCID 15413tert-Butyl methyl etherHCID 668660774-({1-[4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-piperidine-1-carboxylic acid tert-butyl ester

Product 1

HCID 668666464-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylic acid piperidin-4-ylamide hydrochloride

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
80 °C

Procedure

4-({1-[4-(5-Cyclopropylmethoxy-1,3-benzodioxol-4-yl)-5H-pyrrolo[3,2-d]pyrimidin-7-yl]-methanoyl}-amino)-piperidine-1-carboxylic acid tert-butyl ester from example A86 (4.02 g; 7.5 mmol) is dissolved in warm (40-70° C.) 2-propanol (37.5 mL). After addition of 4M HCl in dioxane (7.5 mL) the stirred reaction mixture is heated to 80° C. for two hours. Tert-butylmethylether (150 mL) is added to the reaction mixture while still warm (40-70° C.). After cooling in an ice bath the precipitated product is collected, washed with tert-butylmethylether and dried in high vacuo at 50° C. to yield 3.35 g of the title compound as bright yellow solid.

Workup

  1. customthe stirred reaction mixture
  2. temperaturewhile still warm (40-70° C.)
  3. temperatureAfter cooling in an ice bath the precipitated product
  4. customis collected
  5. washwashed with tert-butylmethylether
  6. customdried in high vacuo at 50° C.

Sources & evidence

ORD record
ord-482a9511c9bf43129be33362392398a9
Source dataset
uspto-grants-2013_05
Patent number
US08445501B2

Reaction notes

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