Diisopropylethylamine → HCID 67494547, compound

HRID 2047154Notes

Reaction equation

HRID 2047154 reaction equation
Cl[C:2]1[CH:7]=[C:6]([N:8](COCC[Si](C)(C)C)COCC[Si](C)(C)C)[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=1.[NH:38]1[CH2:44][CH2:43][C:42](=[O:45])[NH:41][CH2:40][CH2:39]1.C(N(C(C)C)C(C)C)C>CN1C(=O)CCC1>[NH2:8][C:6]1[N:5]2[N:25]=[CH:26][C:27]([C:28]3[CH:29]=[N:30][C:31]4[C:36]([CH:37]=3)=[CH:35][CH:34]=[CH:33][CH:32]=4)=[C:4]2[N:3]=[C:2]([N:38]2[CH2:44][CH2:43][C:42](=[O:45])[NH:41][CH2:40][CH2:39]2)[CH:7]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27372641,4-Diazepan-5-oneHCID 86664780(5-Chloro-3-quinolin-3-yl-pyrazolo[1,5-a]pyrimidin-7-yl)-bis-(2-trimethylsilanyl-ethoxymethyl)-amine

Product 1

HCID 67494547HCID 67494547, compoundYield 96.2%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
185 °C

Procedure

A mixture of 5-chloro-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)-pyrazolo-[1,5-a]pyrimidin-7-amine (50 mg, 0.09 mmoL), 1,4-diazepan-5-one (36 mg, 0.32 mmoL), EtN(iPr)2 (110 uL, 0.63 mmoL) in NMP (0.8 mL) was heated at 185° C. under microwave condition for 45 min. Purification by prep-LC afforded titled compound (32.3 mg, 85%) as its formic acid salt. LCMS tR=2.49 Min. Mass calculated for, M+ 373.1, observed LC/MS m/z 374.1 (M+H).

Workup

  1. customPurification

Sources & evidence

ORD record
ord-bca96234808d4f119c529edd9f42dd5e
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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