1,3-Dimethyl-1H-pyrazol-5-amine → 4-[2-Bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl]-2-fluoro-benzonitrile

HRID 2204348Notes

Reaction equation

HRID 2204348 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]([C:22]#[N:23])=[C:18]([F:24])[CH:17]=1)O)=[O:4].[NH2:25][C:26]1[CH:27]=[C:28]([Cl:34])[C:29](=[O:33])[N:30]([CH3:32])[CH:31]=1.COC(C1C=C(Br)N(C(C)C)C=1C(C1C=CC(C#N)=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]([CH3:13])[CH3:12])[C:6]2[CH:14]([C:16]3[CH:21]=[CH:20][C:19]([C:22]#[N:23])=[C:18]([F:24])[CH:17]=3)[N:25]([C:26]3[CH:27]=[C:28]([Cl:34])[C:29](=[O:33])[N:30]([CH3:32])[CH:31]=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 867031545-bromo-2-[(4-cyano-3-fluoro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl esterHCID 867031555-bromo-2-[(4-cyano-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester

Product 1

HCID 867031534-[2-Bromo-5-(5-chloro-1-methyl-6-oxo-1,6-dihydro-pyridin-3-yl)-1-isopropyl-4-oxo-1,4,5,6-tetrahydro-pyrrolo[3,4-b]pyrrol-6-yl]-2-fluoro-benzonitrile

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared in analogy to the procedure described for Intermediate AX but in the step corresponding to Step AX1, 5-bromo-2-[(4-cyano-3-fluoro-phenyl)-hydroxy-methyl]-1-isopropyl-1H-pyrrole-3-carboxylic acid methyl ester (Step BC1) and 5-amino-3-chloro-1-methyl-1H-pyridin-2-one (Step E5) were used instead of 5-bromo-2-[(4-cyano-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 yellow solid. tR: 1.08 min (HPLC 3); ESI-MS: tR=0.99 min, [M+H]+ 503/505/507 (LC-MS 1); TLC: Rf=0.18 (EtOAc).

Workup

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

Sources & evidence

ORD record
ord-dcbc8ffcdfc7466491cc6536171eba63
Source dataset
uspto-grants-2016_06
Patent number
US09365576B2

Reaction notes

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