2-Methylindoline → 5-(4-(2-methylindoline-1-carbonyl)pyridin-2-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo-[2,3-b]pyridin]-2'(1'H)-one

HRID 1640288Notes

Reaction equation

HRID 1640288 reaction equation
[O:1]=[C:2]1[NH:10][C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]21[CH2:18][C:17]1[C:12](=[CH:13][CH:14]=[C:15]([NH:19][C:20]3[CH:21]=[C:22]([CH:26]=[CH:27][N:28]=3)[C:23]([OH:25])=O)[CH:16]=1)[CH2:11]2.[CH3:29][CH:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:31]1.CCN(C(C)C)C(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F>CN(C=O)C>[CH3:29][CH:30]1[CH2:38][C:37]2[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=2)[N:31]1[C:23]([C:22]1[CH:26]=[CH:27][N:28]=[C:20]([NH:19][C:15]2[CH:16]=[C:17]3[C:12](=[CH:13][CH:14]=2)[CH2:11][C:3]2([C:4]4[C:5](=[N:6][CH:7]=[CH:8][CH:9]=4)[NH:10][C:2]2=[O:1])[CH2:18]3)[CH:21]=1)=[O:25]

Participants

6

Reactant 4

HCID 233052-MethylindolineHCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 581175232-(2'-Oxo-1,1',2',3-tetrahydrospiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-5-ylamino)isonicotinic acid

Product 1

HCID 498013755-(4-(2-methylindoline-1-carbonyl)pyridin-2-ylamino)-1,3-dihydrospiro[indene-2,3'-pyrrolo-[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

150 mg (0.40 mmol) 2-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)isonicotinic acid, 55 μL (0.42 mmol) 2-methylindoline, 0.15 mL (0.87 mmol) DIPEA and 130 mg (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised.

Workup

  1. customThe purification

Sources & evidence

ORD record
ord-797f87507cf241dc8524d56b81a1708d
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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