Diisopropylethylamine → HCID 86650049, compound

HRID 1916400Notes

Reaction equation

HRID 1916400 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:12][CH2:11][CH2:10][C@H:9]1[C@H:13]([C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[C:19]([F:27])[CH:18]=1)[C:14](O)=[O:15])=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.Cl.[CH3:30][C@H:31]1[C:39]2[C:38]([N:40]3[CH2:45][CH2:44][NH:43][CH2:42][CH2:41]3)=[N:37][CH:36]=[N:35][C:34]=2[C@H:33]([OH:46])[CH2:32]1.C(N(C(C)C)CC)(C)C.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>ClCCl>[F:27][C:19]1[CH:18]=[C:17]([C@@H:13]([C@@H:9]2[CH2:10][CH2:11][CH2:12][N:8]2[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C:14]([N:43]2[CH2:42][CH2:41][N:40]([C:38]3[C:39]4[C@H:31]([CH3:30])[CH2:32][C@@H:33]([OH:46])[C:34]=4[N:35]=[CH:36][N:37]=3)[CH2:45][CH2:44]2)=[O:15])[CH:22]=[CH:21][C:20]=1[C:23]([F:26])([F:24])[F:25]

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66618034(5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol dihydrochlorideHCID 66845563HCID 66845563, compound

Product 1

HCID 86650049HCID 86650049, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(S)-2-((S)-1-(tert-Butoxycarbonyl)pyrrolidin-2-yl)-2-(3-fluoro-4-(trifluoromethyl)phenyl)acetic acid (0.036 g, 0.092 mmol) and (5R,7R)-5-methyl-4-(piperazin-1-yl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-7-ol di-hydrochloride (0.028 g, 0.092 mmol) were slurried in dichloromethane (5 mL) and then treated with diisopropylethylamine (0.06 mL, 0.34 mmol). This was followed by treatment with HBTU (0.036 g, 0.095 mmol). The mixture was stirred at ambient temperature for 1 hour. The reaction was concentrated in vacuo and purified by column chromatography, eluting with ethyl acetate. (0.040 g, 72% yield). MS (APCI+) [M+H] 608.2.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. custompurified by column chromatography
  3. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f48e0f6eaf9c484b934f6bd6833673be
Source dataset
uspto-grants-2013_12
Patent number
US08618097B2

Reaction notes

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