Ethyl pyridazine-3-carboxylate → 3-Cyano-4-[2-fluoro-4-(thiazol-2-yloxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl ester

HRID 1796669Notes

Reaction equation

HRID 1796669 reaction equation
C(OC(C1N=NC=CC=1)=O)C.[F:12][C:13]1[CH:18]=[C:17]([O:19][C:20]2[S:21][CH:22]=[CH:23][N:24]=2)[CH:16]=[CH:15][C:14]=1[NH2:25].[CH2:26]([O:28][C:29]([C:31]1[C:32]([CH3:57])=[C:33]2[C:38](NC3C=CC(SC4N(C)C=CN=4)=C(Cl)C=3)=[C:37]([C:54]#[N:55])[CH:36]=[N:35][N:34]2[CH:56]=1)=[O:30])[CH3:27]>>[CH2:26]([O:28][C:29]([C:31]1[C:32]([CH3:57])=[C:33]2[C:38]([NH:25][C:14]3[CH:15]=[CH:16][C:17]([O:19][C:20]4[S:21][CH:22]=[CH:23][N:24]=4)=[CH:18][C:13]=3[F:12])=[C:37]([C:54]#[N:55])[CH:36]=[N:35][N:34]2[CH:56]=1)=[O:30])[CH3:27]

Participants

4

Reactant 3

HCID 14452007Ethyl pyridazine-3-carboxylateHCID 21025108HCID 21025108, compoundHCID 221797212-Fluoro-4-(thiazol-2-yloxy)-phenylamine

Product 1

HCID 210251123-Cyano-4-[2-fluoro-4-(thiazol-2-yloxy)-phenylamino]-5-methyl-pyrrolo[1,2-b]pyridazine-6-carboxylic acid ethyl esterYield 83%

Procedure

Compound 427 (361 mg, 83%) was prepared from 4-chloro-3-cyano-5-methyl-pyrrolo]1,2-b]pyridazine-6-carboxylic acid ethyl ester (Example 1D) (264 mg, 1.0 mmol) and 427B (210 mg, 1.0 mmol) by a route analogous to that used for the preparation of compound 426. It is a dim yellow solid and has a retention time of 6.76 min (standard LC1 method, 8 min run). MS Found: (M+H)+=438.1

Workup

  1. customa retention time of 6.76 min (standard LC1 method, 8 min run)

Sources & evidence

ORD record
ord-32174ec3e4044f8ca7fb3a7bbd259020
Source dataset
uspto-grants-2006_04
Patent number
US07030112B2

Reaction notes

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