Diisopropylethylamine → HCID 178425094, compound

HRID 573143Notes

Reaction equation

HRID 573143 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][C:12](=[O:52])[C:13]2[CH:18]=[CH:17][C:16]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH2:31][CH2:30][C:29]([CH3:33])([CH3:32])[CH2:28][C:27]=4[C:34]4[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=4)[CH2:21][CH2:20]3)=[CH:15][C:14]=2[O:41][C:42]2[CH:43]=[C:44]3[C:48](=[CH:49][C:50]=2[F:51])[NH:47][CH:46]=[CH:45]3)(=[O:10])=[O:9])=[CH:4][C:3]=1[N+:53]([O-:55])=[O:54].[NH2:56][CH2:57][C@H:58]1[CH2:63][CH2:62][C@H:61]([OH:64])[CH2:60][CH2:59]1.C(N(C(C)C)C(C)C)C>O1CCOCC1>[Cl:40][C:37]1[CH:36]=[CH:35][C:34]([C:27]2[CH2:28][C:29]([CH3:32])([CH3:33])[CH2:30][CH2:31][C:26]=2[CH2:25][N:22]2[CH2:21][CH2:20][N:19]([C:16]3[CH:17]=[CH:18][C:13]([C:12]([NH:11][S:8]([C:5]4[CH:6]=[CH:7][C:2]([NH:56][CH2:57][C@H:58]5[CH2:63][CH2:62][C@H:61]([OH:64])[CH2:60][CH2:59]5)=[C:3]([N+:53]([O-:55])=[O:54])[CH:4]=4)(=[O:10])=[O:9])=[O:52])=[C:14]([O:41][C:42]4[CH:43]=[C:44]5[C:48](=[CH:49][C:50]=4[F:51])[NH:47][CH:46]=[CH:45]5)[CH:15]=3)[CH2:24][CH2:23]2)=[CH:39][CH:38]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 67227624HCID 67227624, compoundHCID 178511287HCID 178511287, compound

Product 1

HCID 178425094HCID 178425094, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of EXAMPLE 240A (153 mg), trans-4-(aminomethyl)cyclohexanol (73.5 mg) and N-ethyl-N-isopropylpropan-2-amine (0.16 mL) in dioxane (2 mL) was heated at 100° C. for 20 hours and concentrated. The residue was dissolved in dimethylsulfoxide-methanol (1:1) and purified by HPLC, eluting with 40%-65% acetonitrile in 0.1% TFA water over 40 minutes to provide the title compound. 1H NMR (500 MHz, dimethylsulfoxide-d6) δ 11.22 (s, 2H), 8.56-8.62 (m, 2H), 7.85 (dd, 1H), 7.51 (d, 1H), 7.38 (t, 1H), 7.29-7.36 (m, 4H), 7.12 (d, 1H), 7.03 (d, 2H), 6.66 (dd, 1H), 6.41 (s, 1H), 6.09 (d, 1H), 4.51 (d, 1H), 3.24 (t, 2H), 3.03 (s, 4H), 2.74 (s, 2H), 2.16 (d, 6H), 1.95 (s, 2H), 1.83 (d, 2H), 1.74 (d, 2H), 1.56 (dd, 1H), 1.38 (t, 2H), 0.95-1.16 (m, 4H), 0.92 (s, 6H).

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in dimethylsulfoxide-methanol (1:1)
  3. custompurified by HPLC
  4. washeluting with 40%-65% acetonitrile in 0.1% TFA water over 40 minutes

Sources & evidence

ORD record
ord-9a9c2e9193a44f638e8a3af65f0b54e7
Source dataset
uspto-grants-2015_05
Patent number
US09029404B2

Reaction notes

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