Diisopropylethylamine → HCID 86761382, compound

HRID 1669403Notes

Reaction equation

HRID 1669403 reaction equation
CCN(C(C)C)C(C)C.Cl[CH2:11][CH2:12][N:13]([CH3:51])[C@@H:14]1[CH2:21][N:20]2[C:22]3[CH:23]=[C:24]([C:35]([NH:37][S:38]([N:41]4[CH2:46][CH2:45][NH:44][CH2:43][CH2:42]4)(=[O:40])=[O:39])=[O:36])[CH:25]=[CH:26][C:27]=3[C:28]([CH:29]3[CH2:34][CH2:33][CH2:32][CH2:31][CH2:30]3)=[C:19]2[C:18]2[CH:47]=[CH:48][CH:49]=[CH:50][C:17]=2[O:16][CH2:15]1>CC#N>[CH:29]1([C:28]2[C:27]3[CH:26]=[CH:25][C:24]4=[CH:23][C:22]=3[N:20]3[CH2:21][C@H:14]([CH2:15][O:16][C:17]5[C:18]([C:19]=23)=[CH:47][CH:48]=[CH:49][CH:50]=5)[N:13]([CH3:51])[CH2:12][CH2:11][N:44]2[CH2:43][CH2:42][N:41]([CH2:46][CH2:45]2)[S:38](=[O:40])(=[O:39])[NH:37][C:35]4=[O:36])[CH2:30][CH2:31][CH2:32][CH2:33][CH2:34]1

Participants

4

Reactant 2

HCID 81531DiisopropylethylamineHCID 67343281HCID 67343281, compound

Product 1

HCID 86761382HCID 86761382, compoundYield 26%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

DIPEA (20 eq) was added to a solution of (7R)-7-[(2-chloroethyl)(methyl)amino]-14-cyclohexyl-N-(piperazin-1-ylsulfonyl)-7,8-dihydro-6H-indolo[1,2-e][1,5]benzoxazocine-11-carboxamide (0.001 M) in MeCN and the mixture irradiated in a microwave (SmithCreator) at 150° C. for 5 mins. The volatiles were removed in vacuo and the residue purified by RP-HPLC, eluting with MeCN/TFA buffered with 0.1% TFA gradient. Fractions containing the product were combined and freeze dried to afford the product as a white powder (26% overall for steps 2 through to 6). 1H NMR (600 MHz, DMSO-d6+TFA, 330 K) δ 1.12-1.20 (m, 1H), 1.29-1.37 (m, 2H), 1.47-1.49 (m, 1H), 1.68-1.72 (m, 2H), 1.82-1.99 (m, 4H), 2.43 (s, 3H), 2.69-2.74 (m, 1H), 2.96-2.99 (m, 1H), 3.12-3.19 (m, 1H), 3.31-3.61 (m, 8H), 3.71-3.89 (m, 2H), 4.03-4.07 (m, 1H), 4.11-4.18 (m, 2H), 4.52-4.58 (m, 1H), 4.62-4.68 (m, 1H), 7.32-7.35 (m, 2H), 7.40-7.42 (m, 1H), 7.48 (d, J 8.4, 1H), 7.55-7.58 (m, 1H), 7.91 (d, J 8.4, 1H), 7.95 (s, 1H); (ES+) m/z 592 (M+H)+.

Workup

  1. customthe mixture irradiated in a microwave (SmithCreator) at 150° C. for 5 mins
  2. customThe volatiles were removed in vacuo
  3. customthe residue purified by RP-HPLC
  4. washeluting with MeCN/TFA
  5. additionFractions containing the product
  6. customfreeze dried

Sources & evidence

ORD record
ord-faaf28dbf7e64120819a6aae09b2f977
Source dataset
uspto-grants-2011_08
Patent number
US07989438B2

Reaction notes

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