Diisopropylethylamine → 5-(6-(2,3-dihydro-1H-pyrrolo[3,2-c]pyridin-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydro-spiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 1640281Notes

Reaction equation

HRID 1640281 reaction equation
Cl.[O:2]=[C:3]1[NH:11][C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[C:4]21[CH2:19][C:18]1[C:13](=[CH:14][CH:15]=[C:16]([NH:20][C:21]3[N:26]=[CH:25][N:24]=[C:23]([C:27]([OH:29])=O)[CH:22]=3)[CH:17]=1)[CH2:12]2.[NH:30]1[C:38]2[CH:37]=[CH:36][N:35]=[CH:34][C:33]=2[CH2:32][CH2:31]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.O>[N:30]1([C:27]([C:23]2[N:24]=[CH:25][N:26]=[C:21]([NH:20][C:16]3[CH:17]=[C:18]4[C:13](=[CH:14][CH:15]=3)[CH2:12][C:4]3([C:5]5[C:6](=[N:7][CH:8]=[CH:9][CH:10]=5)[NH:11][C:3]3=[O:2])[CH2:19]4)[CH:22]=2)=[O:29])[C:38]2[CH:37]=[CH:36][N:35]=[CH:34][C:33]=2[CH2:32][CH2:31]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 124909791H,2H,3H-pyrrolo(3,2-c)pyridineHCID 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 498010905-(6-(2,3-dihydro-1H-pyrrolo[3,2-c]pyridin-1-carbonyl)pyrimidin-4-ylamino)-1,3-dihydro-spiro[indene-2,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

0.15 g (0.37 mmol) 6-(2′-oxo-1,1′,2′,3-tetrahydrospiro[indene-2,3′-pyrrolo[2,3-b]pyridin]-5-ylamino)pyrimidine-4-carboxylic acid hydrochloride, 45 mg (0.38 mmol) 2,3-dihydro-1H-pyrrolo[3,2-c]pyridine, 0.15 mL (0.87 mmol) DIPEA and 0.13 g (0.41 mmol) TBTU in 1.8 mL DMF were stirred overnight at RT. Then the reaction mixture was mixed with water, the precipitate formed was suction filtered and dissolved in DMF/NMP. The purification was carried out by preparative HPLC-MS. The product-containing fractions were combined and lyophilised. A second purification was carried out by preparative HPLC-MS.

Workup

  1. customthe precipitate formed
  2. filtrationfiltered
  3. dissolutiondissolved in DMF/NMP
  4. customThe purification
  5. customA second purification

Sources & evidence

ORD record
ord-cf910c5585fb4fffa7cd1487b996d1c5
Source dataset
uspto-grants-2012_02
Patent number
US08110575B2

Reaction notes

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