Sodium Carbonate → HCID 178511178, compound

HRID 1628357Notes

Reaction equation

HRID 1628357 reaction equation
C([N:8]([C:34]1[CH:39]=[CH:38][N:37]=[CH:36][CH:35]=1)[C:9]([C@H:11]1[CH2:16][CH2:15][C@H:14]([CH:17]([NH2:33])[CH2:18][C:19]([NH:21][CH2:22][C:23]2([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[CH2:25][CH2:24]2)=[O:20])[CH2:13][CH2:12]1)=[O:10])(OC(C)(C)C)=O.C(O)(C(F)(F)F)=O.C(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[NH2:33][CH:17]([C@H:14]1[CH2:15][CH2:16][C@H:11]([C:9]([NH:8][C:34]2[CH:35]=[CH:36][N:37]=[CH:38][CH:39]=2)=[O:10])[CH2:12][CH2:13]1)[CH2:18][C:19]([NH:21][CH2:22][C:23]1([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[CH2:25][CH2:24]1)=[O:20]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 21863450Trifluoroacetic acid methylene chlorideHCID 178452845HCID 178452845, compound

Product 1

HCID 178511178HCID 178511178, compoundYield 62.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Boc-trans-4-[1-Amino-2-[[[1-(4-chlorophenyl)cyclopropyl]methylamino]carbonyl]ethyl]-N-4-pyridinyl-cyclohexylcarboxamide (2-4) (0.51 g) was dissolved in anhydrous DCM (10 mL). A 20% TFA/CH2Cl2 (10 mL, 2 mL of TFA in 8 mL of anhydrous CH2Cl2) solution was added. The reaction mixture was stirred at RT and monitored by LC/MS. After 60 minutes, the reaction mixture was poured into 20% Na2CO3 (100 mL). The white solid was collected by filtration, and washed with H2O (2×20 mL). The solid was dried under vacuum at <50° C. to give 260 mg (62.6%) of trans-4-[1-Amino-2-[[[1-(4-chlorophenyl)cyclopropyl]methylamino]-carbonyl]ethyl]-N-4-pyridinyl-cyclohexylcarboxamide (2). 99% pure by HPLC (254 nm); MS (ESI) m/z=441.27 [M+H]+ 1H NMR (DMSO-d6) data is depicted in FIG. 21.

Workup

  1. filtrationThe white solid was collected by filtration
  2. washwashed with H2O (2×20 mL)
  3. customThe solid was dried under vacuum at <50° C.

Sources & evidence

ORD record
ord-69ab277a20f74c00b99b396968adfe51
Source dataset
uspto-grants-2014_07
Patent number
US08785648B1

Reaction notes

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