Diisopropylethylamine → HCID 78427899, compound

HRID 2202397Notes

Reaction equation

HRID 2202397 reaction equation
[CH2:1]([C:5]1([OH:11])[CH2:10][CH2:9][NH:8][CH2:7][CH2:6]1)[CH:2]([CH3:4])[CH3:3].[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[C:16]([S:23]([NH:26][C:27]3[CH:35]=[CH:34][C:30]([C:31](O)=[O:32])=[CH:29][CH:28]=3)(=[O:25])=[O:24])[CH:17]=[CH:18][CH:19]=2)[N:14]=1.CN(C(ON1N=NC2C=CC=CC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C>C(Cl)Cl>[NH2:12][C:13]1[CH:22]=[CH:21][C:20]2[C:15](=[C:16]([S:23]([NH:26][C:27]3[CH:35]=[CH:34][C:30]([C:31]([N:8]4[CH2:7][CH2:6][C:5]([OH:11])([CH2:1][CH:2]([CH3:4])[CH3:3])[CH2:10][CH2:9]4)=[O:32])=[CH:29][CH:28]=3)(=[O:25])=[O:24])[CH:17]=[CH:18][CH:19]=2)[N:14]=1

Participants

6

Reactant 4

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 62787598HCID 62787598, compoundHCID 90419031HCID 90419031, compound

Product 1

HCID 78427899HCID 78427899, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 4-isobutylpiperidin-4-ol (70 mg, 0.44 mmol), 4-(2-aminoquinoline-8-sulfonamido)benzoic acid (100 mg, 0.44 mmol), and HBTU (134 mg, 0.53 mmol) in DCM (5 mL) was added DIPEA (1 mL) dropwise at room temperature, and then the mixture was stirred at room temperature for 1 hour. The resulting mixture was concentrated, purified by a standard method to yield the title compound. 1H NMR (CHLOROFORM-d) δ: 8.10-8.20 (m, 1H), 7.89 (d, J=9.1 Hz, 1H), 7.69-7.82 (m, 1H), 7.06-7.26 (m, 5H), 6.80 (d, J=9.1 Hz, 1H), 5.41 (s, 2H), 4.33 (br. s., 1H), 3.41-3.19 (m., 3H), 1.82 (dt, J=12.9, 6.4 Hz, 1H), 1.63-1.46 (m, 4H), 1.40 (d, J=5.9 Hz, 2H), 0.97 (d, J=6.7 Hz, 6H). LCMS (m/z): 483.7 (M+1)+

Workup

  1. concentrationThe resulting mixture was concentrated
  2. custompurified by a standard method

Sources & evidence

ORD record
ord-09c3601a10ec403699f6cf53590b71f2
Source dataset
uspto-grants-2016_06
Patent number
US09365545B2

Reaction notes

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