(5-Carbamoylthiophen-3-yl)boronic acid → 4-[8-(6-Phenylacetylamino-pyridin-3-ylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-thiophene-2-carboxylic acid amide

HRID 1784020Notes

Reaction equation

HRID 1784020 reaction equation
COC1C=C(NC2C3N(N=CN=3)C(C3C=NNC=3)=CN=2)C=CC=1C(NCC1C=NC(C)=CC=1)=O.Br[C:36]1[N:41]2[N:42]=[CH:43][N:44]=[C:40]2[C:39]([NH:45][C:46]2[CH:47]=[CH:48][C:49]([NH:52][C:53](=[O:61])[CH2:54][C:55]3[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=3)=[N:50][CH:51]=2)=[N:38][CH:37]=1.[NH2:62][C:63]([C:65]1[S:66][CH:67]=[C:68](B(O)O)[CH:69]=1)=[O:64]>>[C:55]1([CH2:54][C:53]([NH:52][C:49]2[N:50]=[CH:51][C:46]([NH:45][C:39]3[C:40]4[N:41]([N:42]=[CH:43][N:44]=4)[C:36]([C:68]4[CH:69]=[C:65]([C:63]([NH2:62])=[O:64])[S:66][CH:67]=4)=[CH:37][N:38]=3)=[CH:47][CH:48]=2)=[O:61])[CH:60]=[CH:59][CH:58]=[CH:57][CH:56]=1

Participants

4

Reactant 3

HCID 67047388(5-Carbamoylthiophen-3-yl)boronic acidHCID 86619666N-[5-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-pyridin-2-yl]-2-phenylacetamideHCID 1359796172-Methoxy-N-(6-methylpyridin-3-yl)methyl-4-[5-(1H-pyrazol-4-yl)-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino]-benzamide

Product 1

HCID 575900204-[8-(6-Phenylacetylamino-pyridin-3-ylamino)-[1,2,4]triazolo[1,5-a]pyrazin-5-yl]-thiophene-2-carboxylic acid amide

Procedure

This compound may be prepared using methods as described for Compound 120, step 4, using N-[5-(5-bromo-[1,2,4]triazolo[1,5-a]pyrazin-8-ylamino)-pyridin-2-yl]-2-phenylacetamide and 2-(aminocarbonyl)thiophene-4-boronic acid. LCMS: Rt 1.06 min (100%) m/z (ESI) 471 (M+H)+.

Workup

  1. customThis compound may be prepared

Sources & evidence

ORD record
ord-de4280073ef14b95aee133186ee3a2e6
Source dataset
uspto-grants-2009_03
Patent number
US07501411B2

Reaction notes

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