4-Bromobenzene-1,2-diamine → HCID 178419324, compound

HRID 1518134Notes

Reaction equation

HRID 1518134 reaction equation
[O:1]1[C:5]2([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]2)[CH2:4][C:3]([C:11](O)=O)=[N:2]1.[Br:14][C:15]1[CH:16]=[C:17]([NH2:22])[C:18]([NH2:21])=[CH:19][CH:20]=1>>[Br:14][C:15]1[CH:20]=[CH:19][C:18]2[NH:21][C:11]([C:3]3[CH2:4][C:5]4([CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]4)[O:1][N:2]=3)=[N:22][C:17]=2[CH:16]=1

Participants

3

Reactant 2

HCID 3235934-Bromobenzene-1,2-diamineHCID 509941141-Oxa-2-azaspiro[4.5]dec-2-ene-3-carboxylic acid

Product 1

HCID 178419324HCID 178419324, compound

Procedure

The title compound was prepared from 1-oxa-2-aza-spiro[4.5]dec-2-ene-3-carboxylic acid (283 mg, 1.55 mmol, as prepared in Example 1, step B) and 4-bromobenzene-1,2-diamine (1.3 eq., 377 mg, 2.02 mmol) in 68% overall yield (299 mg) according to the procedures described in Example 1, steps F and G. 1H-NMR (400 MHz, d4-MeOH) δ: 7.74 (s, 1H), 7.51 (d, J=8.6 Hz, 1H), 7.40 (dd, J=8.6, 1.8 Hz, 1H), 3.25 (s, 2H), 1.69-1.88 (m, 6H), 1.43-1.63 (m, 4H).

Workup

  1. customoverall yield (299 mg)

Sources & evidence

ORD record
ord-37b72d5db4b54776a3c619e065d35b7e
Source dataset
uspto-grants-2012_07
Patent number
US08232409B2

Reaction notes

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