Formaldehyde → HCID 25196610, compound

HRID 2067892Notes

Reaction equation

HRID 2067892 reaction equation
[F:1][CH:2]([F:38])[O:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([CH:23]([CH2:36][OH:37])[C:24]([N:26]4[CH2:31][CH2:30][NH:29][CH:28]([C:32]([F:35])([F:34])[F:33])[CH2:27]4)=[O:25])=[CH:19][CH:18]=3)=[N:14][CH:15]=2)=[CH:6][CH:5]=1.F[CH:40](F)OC1C=CC(C2C=NC(NC3C=CC(C(CO)C(NCCF)=O)=CC=3)=NC=2)=CC=1.C=O.[O-]S([O-])(=O)=O.[Na+].[Na+]>C(Cl)Cl>[F:38][CH:2]([F:1])[O:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH:11]=[N:12][C:13]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([CH:23]([CH2:36][OH:37])[C:24]([N:26]4[CH2:31][CH2:30][N:29]([CH3:40])[CH:28]([C:32]([F:35])([F:34])[F:33])[CH2:27]4)=[O:25])=[CH:21][CH:22]=3)=[N:14][CH:15]=2)=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 24436Sodium SulfateHCID 25195941HCID 25195941, compoundHCID 58542308HCID 58542308, compound

Product 1

HCID 25196610HCID 25196610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)-1-(3-(trifluoromethyl)piperazin-1-yl)-3-hydroxypropan-1-one C37 (prepared as described for C1, 0.05 mmol), HCHO (0.15 mmol, 30% aqueous) and anhydrous Na2SO4 (1.5 mmol) in DCM (2 mL) is stirred at rt for 30 min. Then NaHB(OAc)3 (0.3 mmol) is added and the resulting mixture is stirred for 12 h. Purification by prep-HPLC (ACN gradient 10-70%) affords 2-(4-(5-(4-(difluoromethoxy)phenyl)pyrimidin-2-ylamino)phenyl)-1-(3-(trifluoromethyl)-4-methylpiperazin-1-yl)-3-hydroxypropan-1-one C38. MS (m/z) (M+1)+: 552.2.

Workup

  1. stirringthe resulting mixture is stirred for 12 h
  2. customPurification by prep-HPLC (ACN gradient 10-70%)

Sources & evidence

ORD record
ord-61bf00d27aa64df99ca372c20f3f7abb
Source dataset
uspto-grants-2012_10
Patent number
US08293757B2

Reaction notes

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