Trifluoroacetic acid → HCID 59199262, compound

HRID 2079649Notes

Reaction equation

HRID 2079649 reaction equation
C(O)(C(F)(F)F)=O.[NH:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[C:22]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:34])=[O:33])=[CH:28][CH:27]=2)[N:21]=[CH:20]3)[CH2:10][CH2:9]1.[CH:36](=O)[CH:37]([CH3:39])[CH3:38].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl.C(O)(=O)C>[CH2:36]([N:8]1[CH2:9][CH2:10][CH:11]([O:14][C:15]2[CH:16]=[CH:17][CH:18]=[C:19]3[C:24]=2[N:23]=[C:22]([NH:25][C:26]2[CH:31]=[CH:30][C:29]([S:32]([NH2:35])(=[O:33])=[O:34])=[CH:28][CH:27]=2)[N:21]=[CH:20]3)[CH2:12][CH2:13]1)[CH:37]([CH3:39])[CH3:38]

Participants

7

Reactant 4

HCID 6422Trifluoroacetic acidHCID 6561IsobutyraldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 59199316HCID 59199316, compound

Product 1

HCID 59199262HCID 59199262, compoundYield 80%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of the TFA salt of 4-(8-(piperidin-4-yloxy)quinazolin-2-ylamino)benzenesulfonamide in DCM was added isobutyraldehyde (2 eq) and a few drops of acetic acid. The mixture was stirred for 10 mins and to it was added sodiumtriacetoxyborohydride (1.5 eq) and the mixture was stirred for 1 h. The reductive amination went to completion, by LC/MS. The crude mixture was concentrated and purified on prep HPLC to give the product 4-(8-(1-isobutylpiperidine-4-yloxy)quinazolin-2-ylamino)benzenesulfonamide in 80% yield. ES/MS m/z 456.2 (MH+).

Workup

  1. stirringthe mixture was stirred for 1 h
  2. concentrationThe crude mixture was concentrated
  3. custompurified on prep HPLC

Sources & evidence

ORD record
ord-f256f102b7ff48a0ac42c2a8d68e02a5
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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