Cesium carbonate → HCID 86699692, compound

HRID 1487240Notes

Reaction equation

HRID 1487240 reaction equation
Cl[C:2]1[C:3]2[CH:25]([CH3:26])[CH2:24][N:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:4]=2[N:5]=[C:6]([NH:8][C:9]2[CH:14]=[CH:13][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:11][C:10]=2[O:21][CH3:22])[N:7]=1.[NH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=1[S:43]([NH:46][CH3:47])(=[O:45])=[O:44].C(=O)([O-])[O-].[Cs+].[Cs+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:22][O:21][C:10]1[CH:11]=[C:12]([N:15]2[CH2:20][CH2:19][O:18][CH2:17][CH2:16]2)[CH:13]=[CH:14][C:9]=1[NH:8][C:6]1[N:7]=[C:2]([NH:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=2[S:43]([NH:46][CH3:47])(=[O:45])=[O:44])[C:3]2[CH:25]([CH3:26])[CH2:24][N:23]([CH2:27][C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)[C:4]=2[N:5]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 11328402-amino-N-methylbenzene-1-sulfonamide2×HCID 86699693HCID 86699693, compound

Product 1

HCID 86699692HCID 86699692, compoundYield 91.4%

Reagents, catalysts & solvents 1

HCID 9811564Bis(dibenzylideneacetone)palladiumCatalyst

Conditions

Temperature
130 °C

Procedure

According to General Protocol II, (±)-2-(2-(2-methoxy-4-morpholinophenylamino)-7-(4-methoxybenzyl)-5-methyl-6,7-dihydro-5H-pyrrolo[2,3-a]pyrimidin-4-ylamino)-N-methylbenzenesulfonamide was prepared from (±)-4-chloro-N-(2-methoxy-4-morpholinophenyl)-7-(4-methoxybenzyl)-5-methyl-6,7-dihydro-5H-pyrrolo[2,3-d]pyrimidin-2-amine (80 mg, 0.161 mmol), 2-amino-N-methylbenzenesulfonamide (Intermediate C4, 36 mg, 0.194 mmol), Pd2(dba)3 (15 mg, 0.016 mmol), (±)-BINAP (20 mg, 0.032 mmol) and cesium carbonate (105 mg, 0.322 mmol) heated at 130° C. in a sealed tube for 12 hours, and isolated as a solid (95 mg, yield 91%). 1H NMR (400 MHz, CDCl3) δ ppm 8.32-8.38 (dd, 2H, J=8.4 Hz, 15.2 Hz), 8.00 (s, 1H), 7.85-7.87 (dd, 1H, J=1.6 Hz, 8.0 Hz), 7.50-7.54 (m, 1H), 7.22-7.27 (m, 3H), 7.07-7.10 (t, 1H, J=8.0 Hz), 6.86-6.88 (m, 2H), 6.52-6.53 (d, 1H, J=2.4 Hz), 6.40-6.43 (dd, 1H, J=1.2 Hz, 8.8 Hz), 4.49-4.60 (m, 2H), 4.44-4.46 (m, 1H), 3.87-3.89 (m, 7H), 3.81 (s, 3H), 3.54-3.59 (m, 1H), 3.27-3.28 (m, 1H), 3.09-3.11 (t, 4H, J=4.4 Hz), 2.99-3.02 (dd, 1H, J=4.0 Hz, 9.6 Hz 2.59-2.61 (d, 3H, J=5.6 Hz), 1.22-1.28 (m, 3H).

Sources & evidence

ORD record
ord-8d3059e17c4b472ba97c609f56ebbc66
Source dataset
uspto-grants-2016_08
Patent number
US09428508B2

Reaction notes

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