Hydrochloric Acid → HCID 67956768, compound

HRID 2208253Notes

Reaction equation

HRID 2208253 reaction equation
[CH:1]1([CH2:4][O:5][C:6]2[CH:11]=[CH:10][C:9]([C:12]3([CH3:17])OCC[O:13]3)=[CH:8][C:7]=2[C:18]2[C:19]3[NH:26][C:25]([CH3:27])=[C:24]([C:28]([NH:30][CH:31]4[CH2:36][CH2:35][N:34](C(OC(C)(C)C)=O)[CH2:33][CH2:32]4)=[O:29])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH2:3][CH2:2]1.[ClH:44]>CC(C)=O.O1CCOCC1>[ClH:44].[C:12]([C:9]1[CH:10]=[CH:11][C:6]([O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)=[C:7]([C:18]2[C:19]3[NH:26][C:25]([CH3:27])=[C:24]([C:28]([NH:30][CH:31]4[CH2:36][CH2:35][NH:34][CH2:33][CH2:32]4)=[O:29])[C:20]=3[N:21]=[CH:22][N:23]=2)[CH:8]=1)(=[O:13])[CH3:17]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86666673HCID 86666673, compound

Product 1

HCID 67956768HCID 67956768, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 312751,4-DioxaneSolvent

Procedure

tert-Butyl 4-[({4-[2-(cyclopropylmethoxy)-5-(2-methyl-1,3-dioxolan-2-yl)phenyl]-6-methyl-5H-pyrrolo[3,2-d]pyrimidin-7-yl}carbonyl)amino]piperidine-1-carboxylate from example D.e55 (1.77 g; 2.99 mmol) is dissolved in dry acetone (30 mL). After addition of 4M HCl in dioxane (3 mL) the stirred mixture is gently refluxed until the starting material is consumed according to LC-MS. At ambient temperature the product is precipitated by addition of tert.-butyl methyl ether, isolated by suction filtration, washed with several portions of tert.-butyl methyl ether and dried in high vacuo at 40° C. to yield 1.40 g of the title compound as pale yellow solid.

Workup

  1. temperatureis gently refluxed until the starting material
  2. customis consumed
  3. customAt ambient temperature the product is precipitated by addition of tert.-butyl methyl ether
  4. customisolated by suction filtration
  5. washwashed with several portions of tert.-butyl methyl ether
  6. customdried in high vacuo at 40° C.

Sources & evidence

ORD record
ord-610d5d5a332b42f69180f79fede52a3e
Source dataset
uspto-grants-2016_06
Patent number
US09376442B2

Reaction notes

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