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Diisopropylethylamine → HCID 178476854, compound

HRID 1948084
Notes
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Reaction equation

HRID 1948084 reaction equation
CCCP(O)(O)=O.CCN(C(C)C)C(C)C.[CH2:17]([O:19][P:20]([CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33]2[N:38]=[C:37]([NH:39][C:40]3[CH:41]=[CH:42][C:43]([C@@H:51]4[CH2:56][CH2:55][C@H:54]([C:57]([OH:59])=O)[CH2:53][CH2:52]4)=[C:44]4[C:48]=3[C:47](=[O:49])[N:46]([CH3:50])[CH2:45]4)[C:36]([C:60]([F:63])([F:62])[F:61])=[CH:35][N:34]=2)=[C:28]([O:64][CH3:65])[CH:27]=1)([O:22][CH2:23][CH3:24])=[O:21])[CH3:18].Cl.[NH2:67][OH:68]>CN(C=O)C>[OH:68][NH:67][C:57]([C@@H:54]1[CH2:55][CH2:56][C@H:51]([C:43]2[CH:42]=[CH:41][C:40]([NH:39][C:37]3[C:36]([C:60]([F:63])([F:61])[F:62])=[CH:35][N:34]=[C:33]([NH:32][C:29]4[CH:30]=[CH:31][C:26]([CH2:25][P:20](=[O:21])([O:19][CH2:17][CH3:18])[O:22][CH2:23][CH3:24])=[CH:27][C:28]=4[O:64][CH3:65])[N:38]=3)=[C:48]3[C:44]=2[CH2:45][N:46]([CH3:50])[C:47]3=[O:49])[CH2:52][CH2:53]1)=[O:59]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 204484Propylphosphonic acidHCID 443297Hydroxyamine hydrochlorideHCID 178476855HCID 178476855, compound

Product 1

HCID 178476854HCID 178476854, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent
2×

Procedure

To 50% 1-propylphosphonic acid cyclic anhydride in DMF (9.9 μL, 0.017 mmol) were added additional DMF (0.5 mL), DIPEA (9.9 μL, 0.0567 mmol) and 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). The mixture was stirred at room temperature for 30 minutes. Hydroxylamine hydrochloride (2.0 mg, 0.0283 mmol) was added and the mixture was stirred at room temperature overnight. The crude mixture was purified by MDP to obtain the title compound (5.2 mg, 51% yield). 1H NMR (400 MHz, methanol-d4) d ppm 1.29 (t, J=7.1 Hz, 6H), 1.68-1.82 (m, 4H), 2.00-2.16 (m, 4H), 2.52 (br. s., 1H), 2.73 (t, J=11.1 Hz, 1H), 3.19 (s, 3H), 3.38 (d, J=21.7 Hz, 2H), 3.90 (s, 3H), 4.11 (qd, J=7.3, 7.1 Hz, 4H), 4.55 (s, 2H), 6.95-7.04 (m, 1H), 7.14 (s, 1H), 7.39 (br. s., 1H), 7.65 (d, J=8.1 Hz, 1H), 8.33 (br. s., 2H). MS (ES+): m/z 721.19 (100) [MH+]; HPLC: tR=0.97 min (UPLC, purity).

Workup

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

Sources & evidence

ORD record
ord-dc75790516aa40589cc3148f938d4228
Source dataset
uspto-grants-2013_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08399433B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes