1,3-Dimethyl-1H-pyrazol-5-amine → HCID 86703149, compound

HRID 2204346Notes

Reaction equation

HRID 2204346 reaction equation
CO[C:3]([C:5]1[CH:9]=[C:8]([Br:10])[N:7]([CH:11]([CH3:13])[CH3:12])[C:6]=1[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([F:23])[CH:17]=1)O)=[O:4].[NH2:24][C:25]1[CH:26]=[C:27]([Cl:33])[C:28](=[O:32])[N:29]([CH3:31])[CH:30]=1.COC(C1C=C(Br)N(C(C)C)C=1C(C1C=CC(Cl)=CC=1)O)=O.CN1C(N)=CC(C)=N1.ClC(N(C)C)=C(C)C>CCOC(C)=O.CCN(CC)CC>[Br:10][C:8]1[N:7]([CH:11]([CH3:12])[CH3:13])[C:6]2[CH:14]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[C:18]([F:23])[CH:17]=3)[N:24]([C:25]3[CH:26]=[C:27]([Cl:33])[C:28](=[O:32])[N:29]([CH3:31])[CH:30]=3)[C:3](=[O:4])[C:5]=2[CH:9]=1

Participants

8

Reactant 5

HCID 5207211,3-Dimethyl-1H-pyrazol-5-amineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 717560735-Amino-3-chloro-1-methyl-1,2-dihydropyridin-2-oneHCID 867031015-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl esterHCID 86703150HCID 86703150, compound

Product 1

HCID 86703149HCID 86703149, compound

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared in analogy to the procedure described for Intermediate AW but in the step corresponding to Step AW2, 5-bromo-2-[(4-chloro-3-fluoro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step AZ1) and 5-amino-3-chloro-1-methyl-1H-pyridin-2-one (Step E5) were used instead of 5-bromo-2-[(4-chloro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester and 2,5-dimethyl-2H-pyrazol-3-ylamine respectively. Moreover, in this step, the procedures described for Steps H3 and H2 using 1-chloro-N,N,2-trimethylpropenylamine and Et3N were used. The title compound (containing some of the corresponding 2-chloro analog) was obtained as a white foam. tR: 1.18 min (HPLC 3); ESI-MS: tR=1.10 min, [M+H]+ 512/514/516 (LC-MS 1); TLC: Rf=0.19 (EtOAc).

Workup

  1. customThe title compound was prepared in analogy to the procedure
  2. customwas obtained as a white foam

Sources & evidence

ORD record
ord-0d0db51949ec4d19b94ec82c47c6bae8
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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