Triethylamine → 4-[6-(4-Methanesulfonyl-phenylamino)-5-nitro-pyrimidin-4-yloxy]-piperidine-1-carboxylic Acid 2-isopropyl-5-methyl-cyclohexyl Ester

HRID 1036755Notes

Reaction equation

HRID 1036755 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].C(N(CC)CC)C.Cl[C:36]([O:38][CH:39]1[CH:44]([CH:45]([CH3:47])[CH3:46])[CH2:43][CH2:42][CH:41]([CH3:48])[CH2:40]1)=[O:37]>CN(C=O)C>[CH:45]([CH:44]1[CH2:43][CH2:42][CH:41]([CH3:48])[CH2:40][CH:39]1[O:38][C:36]([N:25]1[CH2:26][CH2:27][CH:22]([O:21][C:16]2[C:17]([N+:18]([O-:20])=[O:19])=[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[N:13]=[CH:14][N:15]=2)[CH2:23][CH2:24]1)=[O:37])([CH3:46])[CH3:47]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 151928Menthyl chloroformateHCID 11257886(4-Methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine2×

Product 1

HCID 666738884-[6-(4-Methanesulfonyl-phenylamino)-5-nitro-pyrimidin-4-yloxy]-piperidine-1-carboxylic Acid 2-isopropyl-5-methyl-cyclohexyl Ester

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound A23 was prepared in a similar manner as described above using (4-methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine (i.e., Compound A2) (15 mg, 0.035 mmol), triethylamine (50 μl), menthyl chloroformate (10 mg, 0.046 mmol), DMF (0.6 mL), 1H NMR (CDCl3, 400 MHz) δ 0.81 (d, 3H), 0.92 (d, 6H), 1.06 (m,1H), 1.10 (m, 1H), 1.41 (m, 1H), 1.51 (m, 1H), 1.67 (m,2H), 1.94 (m, 4H), 2.08 (m, 2H), 3.08 (s, 3H), 3.65 (m, 4H), 4.58 (m, 1H), 5.60 (m, 1H), 7.86 (d, 2H), 7.97 (d, 2H), 8.41 (s, 1H), 10.18 (s, 1H). Exact mass calculated for C27H37N5O7S 575.24, found 576.4 (MH+).

Workup

  1. customCompound A23 was prepared in a similar manner

Sources & evidence

ORD record
ord-cdc6b4ba8da5402ea40b5ae5153508aa
Source dataset
uspto-grants-2013_10
Patent number
US08546429B2

Reaction notes

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