Diisopropylethylamine → HCID 18617839, compound

HRID 1264239Notes

Reaction equation

HRID 1264239 reaction equation
[O:1]=[C:2]1[NH:7][CH2:6][CH:5]([C:8]2[CH:16]=[CH:15][C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=2)[CH2:4][CH2:3]1.[NH2:17][CH2:18][CH2:19][C:20]1[CH:21]=[C:22]2[C:26](=[CH:27][CH:28]=1)[NH:25][CH:24]=[C:23]2[C:29]#[N:30].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.C(O)(C(F)(F)F)=O.O.C(O)(C(F)(F)F)=O.C(#N)C>CN(C=O)C>[C:29]([C:23]1[C:22]2[C:26](=[CH:27][CH:28]=[C:20]([CH2:19][CH2:18][NH:17][C:12](=[O:14])[C:11]3[CH:10]=[CH:9][C:8]([CH:5]4[CH2:4][CH2:3][C:2](=[O:1])[NH:7][CH2:6]4)=[CH:16][CH:15]=3)[CH:21]=2)[NH:25][CH:24]=1)#[N:30]

Participants

8

Reactant 6

HCID 81531DiisopropylethylamineHCID 2733084Methanaminium, N-((1H-benzotriazol-1-yloxy)(dimethylamino)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 11217658HCID 11217658, compoundHCID 18617602HCID 18617602, compoundHCID 21924481TFA acetonitrileHCID 22392675Trifluoroacetic acid water

Product 1

HCID 18617839HCID 18617839, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-(6-Oxo-piperidin-3-yl)-benzoic acid (190 mg, 0.87 mmol, reference example 65) and 5-(2-amino-ethyl)-1H-indole-3-carbonitrile (161 mg, 0.87 mmol, reference example 2) is dissolved in anhydrous DMF (3 mL). To this solution is added diisoproplyethylamine (330 μl, 1.9 mmol), followed by HBTU (330 mg, 0.87 mmol) and allowed to stir at room temperature overnight (16 hours). The product is isolated by Reverse-Phase chromatography of the crude reaction mixture (Dynamax C-18 60 A (5×30 cm), 50 ml/min, λ@ 220 nm, 10-70% B in 15 minutes, A: 0.1% TFA/water, B: 0.1% TFA/acetonitrile). 1H NMR (300 MHz, DMSO) δ 1.94 (m, 2H), 2.26 (m, 2H), 2.92 (t, J=7.1, 2H), 3.19 (m, 1H), 3.48 (m, 2H), 3.46 (m, 2H), 7.13 (d, J=8.4, 1H), 7.15 (d, J=1.4, 2H), 7.36 (d, J=8.3, 2H), 7.43 (d, J=8.5, 1H), 7.46 (s, 1H), 7.55 (d, J=2.5, 1H), 7.73 (d, J=8.3, 2H), 8.17 (d, J=3.0, 1H), 8.47 (t, J=5.5, 1H). MS (Ion spray) m/z 387 (M+H)+.

Workup

  1. customThe product is isolated by Reverse-Phase chromatography of the crude
  2. customreaction mixture (Dynamax C-18 60 A (5×30 cm), 50 ml/min, λ@ 220 nm, 10-70% B in 15 minutes

Sources & evidence

ORD record
ord-4fcf2a382dfd4ceeba68e80d9cb7c222
Source dataset
uspto-grants-2003_04
Patent number
US06541505B1

Reaction notes

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