Triethylamine → HCID 86615702, compound

HRID 216204Notes

Reaction equation

HRID 216204 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[N:5]=[C:4]([NH:10][CH2:11][CH2:12][C:13]2[CH:21]=[CH:20][C:16]([C:17]([OH:19])=O)=[CH:15][CH:14]=2)[CH:3]=1.[C:22]([NH:25][NH2:26])(=[O:24])[CH3:23].C(N(CC)CC)C.F[B-](F)(F)F.N1(OC(=[N+](C)C)N(C)C)C2C=CC=CC=2N=N1>CN(C=O)C>[C:22]([NH:25][NH:26][C:17](=[O:19])[C:16]1[CH:15]=[CH:14][C:13]([CH2:12][CH2:11][NH:10][C:4]2[CH:3]=[C:2]([Cl:1])[N:7]=[C:6]([O:8][CH3:9])[N:5]=2)=[CH:21][CH:20]=1)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 14039AcetohydrazideHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 86240122HCID 86240122, compound

Product 1

HCID 86615702HCID 86615702, compoundYield 55.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[2-(6-chloro-2-methoxy-pyrimidin-4-ylamino)-ethyl]-benzoic acid (0.41 g, 1.33 mmol), acetic acid hydrazide (0.1 g, 2 mmol), and triethylamine (0.7 mL, 3.99 mmol) in DMF (3 mL) is added [(benzotriazol-1-yloxy)-dimethylamino-methylene]-dimethyl-ammonium tetrafluoro borate (0.51 g, 1.6 mmol) at room temperature. After 15 h at 20° C., the solid is filtered, and washed with water to afford 4-[2-(6-chloro-2-methoxy-pyrimidin-4-ylamino)-ethyl]-benzoic acid N′-acetyl-hydrazide (267 mg). The filtrate is extracted with EtOAc, and concentrated to afford additional amount of 4-[2-(6-chloro-2-methoxy-pyrimidin-4-ylamino)-ethyl]-benzoic acid N′-acetyl-hydrazide (100 mg). LCMS: RT=2 minutes; MS: 364 (M+H).

Workup

  1. filtrationthe solid is filtered
  2. washwashed with water

Sources & evidence

ORD record
ord-1f4469284e574ada91f7a416c0fefb17
Source dataset
uspto-grants-2012_06
Patent number
US08193183B2

Reaction notes

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