Methanamine, hydrochloride (1:1) → HCID 178476853, compound

HRID 1948083Notes

Reaction equation

HRID 1948083 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][C:10]1[CH:15]=[CH:14][C:13]([NH:16][C:17]2[N:22]=[C:21]([NH:23][C:24]3[CH:25]=[CH:26][C:27]([C@@H:35]4[CH2:40][CH2:39][C@H:38]([C:41](O)=[O:42])[CH2:37][CH2:36]4)=[C:28]4[C:32]=3[C:31](=[O:33])[N:30]([CH3:34])[CH2:29]4)[C:20]([C:44]([F:47])([F:46])[F:45])=[CH:19][N:18]=2)=[C:12]([O:48][CH3:49])[CH:11]=1)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[CH3:50][N:51](C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.[B-](F)(F)(F)F.[Cl-].C[NH3+].CCN(C(C)C)C(C)C>CN(C=O)C>[CH3:49][O:48][C:12]1[CH:11]=[C:10]([CH:15]=[CH:14][C:13]=1[NH:16][C:17]1[N:22]=[C:21]([NH:23][C:24]2[CH:25]=[CH:26][C:27]([C@H:35]3[CH2:36][CH2:37][C@@H:38]([C:41](=[O:42])[NH:51][CH3:50])[CH2:39][CH2:40]3)=[C:28]3[C:32]=2[C:31](=[O:33])[N:30]([CH3:34])[CH2:29]3)[C:20]([C:44]([F:47])([F:46])[F:45])=[CH:19][N:18]=1)[CH2:9][P:4](=[O:5])([O:3][CH2:1][CH3:2])[O:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 11637Methanamine, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 178476855HCID 178476855, compound

Product 1

HCID 178476853HCID 178476853, compoundYield 43.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

cis-4-(7-{[2-({4-[(Diethoxyphosphoryl)methyl]-2-methoxyphenyl}amino)-5-(trifluoromethyl)pyrimidin-4-yl]amino}-2-methyl-1-oxo-2,3-dihydro-1H-isoindol-4-yl)cyclohexanecarboxylic acid (10.0 mg, 0.0142 mmol), TBTU (9.1 mg, 0.0283 mmol) and DMF (0.8 mL) were mixed and the mixture was stirred at room temperature for 30 minutes. Methylammonium chloride (9.6 mg, 0.142 mmol) and DIPEA (24.7 μL, 0.142 mmol) were added and the mixture was stirred at room temperature for 2 hours. The crude was purified by MDP to obtain the title compound (4.4 mg, 43% yield). 1H NMR (400 MHz, methanol-d4) δ=1.29 (t, J=7.1 Hz, 6H), 1.67-1.81 (m, 4H), 1.87-2.01 (m, 2H), 2.15 (d, J=12.4 Hz, 2 H), 2.60 (br. s., 1H), 2.71 (t, J=11.2 Hz, 1H), 2.79 (s, 3H), 3.18 (s, 3H), 3.37 (d, J=21.7 Hz, 2H), 3.90 (s, 3H), 4.10 (quin, J=7.3 Hz, 4H), 4.53 (s, 2H), 6.99 (d, J=7.8 Hz, 1H), 7.13 (s, 1H), 7.34 (br. s., 1H), 7.67 (d, J=8.1 Hz, 1H), 8.33 (br. s., 2H). MS (ES+): m/z 719.36 (100) [MH+]; HPLC: tR=1.04 min (UPLC, purity).

Workup

  1. stirringthe mixture was stirred at room temperature for 2 hours
  2. customThe crude was purified by MDP

Sources & evidence

ORD record
ord-41beb698787249cc99fe93de6c6b979e
Source dataset
uspto-grants-2013_03
Patent number
US08399433B2

Reaction notes

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