Butyl isocyanate → 1-Butyl-3-[2-chloro-3-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-phenyl]-urea

HRID 250618Notes

Reaction equation

[NH2:1][C:2]1[C:3]([Cl:11])=[C:4]([CH:8]=[CH:9][CH:10]=1)[C:5]([OH:7])=O.[N:12]([CH2:15][CH2:16][CH2:17][CH3:18])=[C:13]=[O:14].[N-]=C=O.[N:22]1[CH:27]=[CH:26][CH:25]=[C:24]([C:28]2[CH:29]=[C:30]3[CH:36]=[CH:35][NH:34][C:31]3=[N:32][CH:33]=2)[CH:23]=1>>[CH2:15]([NH:12][C:13]([NH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([C:36]2[C:30]3[C:31](=[N:32][CH:33]=[C:28]([C:24]4[CH:23]=[N:22][CH:27]=[CH:26][CH:25]=4)[CH:29]=3)[NH:34][CH:35]=2)=[O:7])[C:3]=1[Cl:11])=[O:14])[CH2:16][CH2:17][CH3:18]

Participants

Reactant 4

HCID 8110Butyl isocyanate

HCID 105034Isocyanate

HCID 4593153-Amino-2-chlorobenzoic acid

HCID 513585515-(Pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine2×

Product 1

HCID 580862751-Butyl-3-[2-chloro-3-(5-pyridin-3-yl-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-phenyl]-urea

Procedure

Additional compounds were prepared following the protocol of Scheme 57, replacing 3-amino-2-chlorobenzoic acid 586 with an appropriate carboxylic acid and optionally replacing 1-isocyanatobutane with an appropriate isocyanate in Step 1 and optionally replacing 5-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridine 89 with an appropriate substituted 7-azaindole (see Example 17) in Step 2. The following compounds were made following this procedure:

Workup

customAdditional compounds were prepared

Sources & evidence

ORD record: ord-f28720afbd794aa19e8524d53ec14d0a
Source dataset: uspto-grants-2011_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07863288B2

Reaction notes

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