Ethanol → HCID 59743406, compound

HRID 1947019Notes

Reaction equation

HRID 1947019 reaction equation
C(OC(=O)[NH:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([CH:17]2[CH2:22][CH2:21][CH:20]([NH:23][C:24]3[N:29]=[C:28]([N:30]4[C:38]5[C:33](=[C:34]([O:39][CH2:40][CH2:41][CH2:42][S:43]([CH3:46])(=[O:45])=[O:44])[CH:35]=[CH:36][CH:37]=5)[CH:32]=[CH:31]4)[CH:27]=[CH:26][N:25]=3)[CH2:19][CH2:18]2)=[O:16])[CH2:11][CH2:10]1)(C)(C)C.CCO>Cl>[NH2:7][CH2:8][CH:9]1[CH2:14][CH2:13][N:12]([C:15]([CH:17]2[CH2:18][CH2:19][CH:20]([NH:23][C:24]3[N:29]=[C:28]([N:30]4[C:38]5[C:33](=[C:34]([O:39][CH2:40][CH2:41][CH2:42][S:43]([CH3:46])(=[O:44])=[O:45])[CH:35]=[CH:36][CH:37]=5)[CH:32]=[CH:31]4)[CH:27]=[CH:26][N:25]=3)[CH2:21][CH2:22]2)=[O:16])[CH2:11][CH2:10]1

Participants

4

Reactant 2

HCID 702EthanolHCID 69309534HCID 69309534, compound

Product 1

HCID 59743406HCID 59743406, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A solution of [1-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-yl-amino}-cyclohexanecarbonyl)-piperidin-4-ylmethyl]-carbamic acid t-butyl ester (0.827 g, 1.236 mM) in 10 mL of 10% HCl soln./EtOH was briefly heated on a steam bath, stirred for 7 hours at RT, concentrated to half volume and cooled in an ice bath. The light yellow solid was collected by filtration, washed with cold EtOH, and dried at 60° C. in vacuo. The product was extracted into DCM, crystallized from EtOH, and dried in vacuo at 60° C. to yield (4-aminomethyl-piperidin-1-yl)-(4-{4-[4-(3-methanesulfonyl-propoxy)-indol-1-yl]-pyrimidin-2-ylamino}-cyclohexyl)-methanone (Compound 304) as a white solid (0.41 g, mp 124-126° C.).

Workup

  1. concentrationconcentrated to half volume
  2. temperaturecooled in an ice bath
  3. filtrationThe light yellow solid was collected by filtration
  4. washwashed with cold EtOH
  5. customdried at 60° C. in vacuo
  6. extractionThe product was extracted into DCM
  7. customcrystallized from EtOH
  8. customdried in vacuo at 60° C.

Sources & evidence

ORD record
ord-ae3f4104bfa44e76a6ac70f50d2b4ded
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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