1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → HCID 102335872, compound

HRID 595632Notes

Reaction equation

HRID 595632 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH:17]([F:20])[CH2:18][NH2:19])[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3.[CH2:21]([O:24][C:25]1[CH:41]=[CH:40][C:28]([C:29]([C:31]2[CH:39]=[CH:38][C:34]([C:35](O)=[O:36])=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:26]=1)[C:22]#[CH:23].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>CN(C)C=O.CCOC(C)=O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH2:16][CH:17]([F:20])[CH2:18][NH:19][C:35](=[O:36])[C:34]3[CH:33]=[CH:32][C:31]([C:29](=[O:30])[C:28]4[CH:40]=[CH:41][C:25]([O:24][CH2:21][C:22]#[CH:23])=[CH:26][CH:27]=4)=[CH:39][CH:38]=3)[C:7]3[C:12]([C:13]=2[CH:14]=1)=[CH:11][C:10]([Br:15])=[CH:9][CH:8]=3

Participants

7

Reactant 4

HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 53341689HCID 53341689, compoundHCID 71254034HCID 71254034, compound

Product 1

HCID 102335872HCID 102335872, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

3-(3,6-dibromo-9H-carbazol-9-yl)-2-fluoropropan-1-amine (Naidoo et al., 2014) (40.2 mg, 0.10 mmol) was added to a solution of 4-(4-(prop-2-yn-1-yloxy)benzoyl)benzoic acid (Bandyopadhyay et al., 2011) (28.5 mg, 0.10 mmol), N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (21.2 mg, 0.11 mmol) and 1-hydroxybenzotriazole hydrate (15.0 mg, 0.11 mmol) in dimethylformamide (0.4 ml). The reaction went to completion within an hour. The mixture was diluted with EtOAc and washed several times with water and then brine. The organic layer was dried over Na2SO4, filtered and condensed to give a light brown solid in 90% yield. 1H NMR (Acetone-d6, 400 MHz) δ 8.41 (dd, J=2.0, 0.6 Hz, 2H), 8.07 (d, J=8.4 Hz, 2H), 7.82 (dd, J=10.3, 8.6 Hz, 4H), 7.71-7.56 (m, 4H), 7.16 (d, J=8.9 Hz, 2H), 5.39-5.10 (dm, 1H), 4.94 (d, J=2.4 Hz, 2H), 4.91-4.85 (m, 1H), 4.82 (d, J=5.4 Hz, 1H), 4.05-3.89 (m, 1H), 3.87-3.70 (m, 1H), 3.17 (t, J=2.4 Hz, 1H). 13C NMR (CD2Cl2, 100 MHz): 194.6, 167.3, 161.7, 141.4, 140.1, 136.9, 132.8, 130.7, 130.2, 129.7, 127.3, 124.1, 123.6, 114.9, 113.0, 111.2 (JC-F=1.9 Hz), 92.1 (JC-F=176.2 Hz), 78.2, 76.3, 56.4, 45.8 (JC-F=22.5 Hz), 42.3 (JC-F=21.2 Hz). MS (ESI), m/z: calculated 660.01. found 660.7 (M+1).

Workup

  1. waitThe reaction went to completion within an hour
  2. washwashed several times with water
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. customcondensed
  6. customto give a light brown solid in 90% yield

Sources & evidence

ORD record
ord-fc297d372d5547978a45f0855b54459d
Source dataset
uspto-grants-2016_01
Patent number
US09243281B2

Reaction notes

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