1,2-Dichloroethane → HCID 178521728, compound

HRID 1047563Notes

Reaction equation

HRID 1047563 reaction equation
[F:1][C:2]1([F:11])[CH2:7][CH2:6][CH:5]([C:8]([OH:10])=O)[CH2:4][CH2:3]1.C1C=CC2N(O)N=NC=2C=1.C(Cl)CCl.C(=O)(O)[O-].[Na+].[O:31]1[CH2:36][CH2:35][N:34]([C:37]2[CH:38]=[CH:39][C:40]3[N:44]=[C:43]([C:45]4[C:53]5[C:48](=[CH:49][CH:50]=[C:51]([NH2:54])[CH:52]=5)[N:47]([CH:55]5[CH2:60][CH2:59][CH2:58][CH2:57][O:56]5)[N:46]=4)[NH:42][C:41]=3[CH:61]=2)[CH2:33][CH2:32]1>CN(C=O)C>[F:11][C:2]1([F:1])[CH2:3][CH2:4][CH:5]([C:8]([NH:54][C:51]2[CH:52]=[C:53]3[C:48](=[CH:49][CH:50]=2)[N:47]([CH:55]2[CH2:60][CH2:59][CH2:58][CH2:57][O:56]2)[N:46]=[C:45]3[C:43]2[NH:44][C:40]3[CH:39]=[CH:38][C:37]([N:34]4[CH2:35][CH2:36][O:31][CH2:32][CH2:33]4)=[CH:61][C:41]=3[N:42]=2)=[O:10])[CH2:6][CH2:7]1

Participants

7

Reactant 5

HCID 111,2-DichloroethaneHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 27791364,4-Difluorocyclohexanecarboxylic acidHCID 136352262HCID 136352262, compound

Product 1

HCID 178521728HCID 178521728, compoundYield 44.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4,4-Difluorocyclohexanecarboxylic acid (3.92 mg, 0.024 mmol), HOBt (4.84 mg, 0.036 mmol), EDC (6.87 mg, 0.036 mmol) and sodium bicarbonate (2.007 mg, 0.024 mmol) was added to a solution of 3-(6-morpholino-1H-benzo[d]imidazol-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-indazol-5-amine (10 mg, 0.024 mmol) in DMF (5 mL). The reaction mixture was stirred at room temperature for 24 h after and then the solvent was removed in vacuo. Purification by flash column chromatography (6% CH3OH/CH2Cl2) afforded the title compound (6 mg) as a solid. 1H NMR: (400 MHz, CD3OD): δ 8.49 (s, 1H), 7.76-7.70 (m, 2H), 7.57 (d, 1H, J=8.8 Hz), 7.17 (m, 1H), 7.07 (dd, 1H, J=2.0 & 8.8 Hz), 5.90 (dd, 1H, J=2.0 and 9.6 Hz), 4.01 (m, 1H), 3.86 (m, 4H), 3.81 (m, 1H), 3.17 (m, 4H), 2.65 (m, 1H), 2.53 (m, 1H), 2.43 (m, 1H), 2.18-2.10 (m, 2H), 1.99 (m, 3H), 1.92-1.82 (m, 4H), 1.75 (m, 3H); ESI-MS [M+H]+: 565.17.

Workup

  1. customwas removed in vacuo
  2. customPurification by flash column chromatography (6% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-035ab9aca50549c5b913087b0954e95c
Source dataset
uspto-grants-2013_10
Patent number
US08569511B2

Reaction notes

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