Pyridine → 4-{1-[5-(1-Formyl-cyclopropyl)-isoxazol-3-ylcarbamoyl]-1H-indol-5-yloxy}-5,7-dihydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

HRID 1887659Notes

Reaction equation

HRID 1887659 reaction equation
N1C=CC=CC=1.C(N(CC)CC)C.[C:14]([O:18][C:19]([N:21]1[CH2:29][C:28]2[C:27]([O:30][C:31]3[CH:32]=[C:33]4[C:37](=[CH:38][CH:39]=3)[N:36]([C:40](=[O:52])[NH:41][C:42]3[CH:46]=[C:45]([C:47]5([CH2:50][OH:51])[CH2:49][CH2:48]5)[O:44][N:43]=3)[CH:35]=[CH:34]4)=[N:26][CH:25]=[N:24][C:23]=2[CH2:22]1)=[O:20])([CH3:17])([CH3:16])[CH3:15]>C(Cl)Cl.CS(C)=O>[C:14]([O:18][C:19]([N:21]1[CH2:29][C:28]2[C:27]([O:30][C:31]3[CH:32]=[C:33]4[C:37](=[CH:38][CH:39]=3)[N:36]([C:40](=[O:52])[NH:41][C:42]3[CH:46]=[C:45]([C:47]5([CH:50]=[O:51])[CH2:48][CH2:49]5)[O:44][N:43]=3)[CH:35]=[CH:34]4)=[N:26][CH:25]=[N:24][C:23]=2[CH2:22]1)=[O:20])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 3

HCID 1049PyridineHCID 8471TriethylamineHCID 675388064-{1-[5-(1-hydroxymethyl-cyclopropyl)-isoxazol-3-ylcarbamoyl]-1H-indol-5-yloxy}-5,7-dihydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

Product 1

HCID 593941044-{1-[5-(1-Formyl-cyclopropyl)-isoxazol-3-ylcarbamoyl]-1H-indol-5-yloxy}-5,7-dihydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of SO3.pyridine (0.992 g, 6.23 mmol), triethylamine (1.086 mL, 7.79 mmol) and DMSO (1.11 mL, 15.6 mmol) at 0° C., 4-{1-[5-(1-hydroxymethyl-cyclopropyl)-isoxazol-3-ylcarbamoyl]-1H-indol-5-yloxy}-5,7-dihydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester (0.83 g, 1.559 mmol) in DCM (5 mL) and DMSO (1 mL) is added. The reaction is stirred at 0° C. for 2 h. After the reaction is complete, it is quenched with NH4CL, extracted, and evaporated. 4-{1-[5-(1-Formyl-cyclopropyl)-isoxazol-3-ylcarbamoyl]-1H-indol-5-yloxy}-5,7-dihydro-pyrrolo[3,4-d]pyrimidine-6-carboxylic acid tert-butyl ester is then obtained using FCC and eluting with 100:0 heptane:EtOAc to 0:100 Heptane:EtOAc. MS (ESI) m/z 531.0 (M+1).

Workup

  1. customit is quenched with NH4CL
  2. extractionextracted
  3. customevaporated

Sources & evidence

ORD record
ord-7fc446002ad24d4ab759c2f8eef2819d
Source dataset
uspto-grants-2013_08
Patent number
US08501756B2

Reaction notes

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