Dimethylformamide → N-(dicyclopropylmethyl)-N-methyl-6-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo-[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxamide

HRID 1640271Notes

Reaction equation

HRID 1640271 reaction equation
CCN([CH:7]([CH3:9])[CH3:8])C(C)C.CN(C(ON1N=NC2C=C[CH:23]=[CH:24][C:19]1=2)=[N+](C)C)C.[B-](F)(F)(F)F.Cl.[O:33]=[C:34]1[NH:42][C:37]2=[N:38][CH:39]=[CH:40][CH:41]=[C:36]2[C:35]21[CH2:50][C:49]1[C:44](=[CH:45][CH:46]=[C:47]([NH:51][C:52]3[N:57]=[CH:56][N:55]=[C:54]([C:58]([OH:60])=O)[CH:53]=3)[CH:48]=1)[CH2:43]2.[CH3:61][N:62]([CH:64]=O)C>>[CH:23]1([CH:64]([CH:8]2[CH2:7][CH2:9]2)[N:62]([CH3:61])[C:58]([C:54]2[CH:53]=[C:52]([NH:51][C:47]3[CH:48]=[C:49]4[C:44](=[CH:45][CH:46]=3)[CH2:43][C:35]3([C:36]5[C:37](=[N:38][CH:39]=[CH:40][CH:41]=5)[NH:42][C:34]3=[O:33])[CH2:50]4)[N:57]=[CH:56][N:55]=2)=[O:60])[CH2:24][CH2:19]1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 667221856-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-yl-amino)pyrimidine-4-carboxylic acid-hydrochloride

Product 1

HCID 49800516N-(dicyclopropylmethyl)-N-methyl-6-(2'-oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo-[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxamide

Procedure

1.2 equivalents (12 μmol) of the amine derivative, 3.4 equivalents DIPEA (34 μmol) and 1.20 equivalents (12 μmol) TBTU were added to 4.1 mg (10 μmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride in 0.32 mL DMF and the mixture was shaken overnight at RT. The reaction mixture was evaporated down at 60° C. in a vacuum centrifuge. The following compounds were able to be synthesised analogously to this working method:

Workup

  1. customThe reaction mixture was evaporated down at 60° C. in a vacuum centrifuge
  2. customto be synthesised analogously to this working method

Sources & evidence

ORD record
ord-a70baaeca1f0483bb37a3d186ede802d
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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