Sulfamic Acid → HCID 178480875, compound

HRID 1272500Notes

Reaction equation

HRID 1272500 reaction equation
[NH2:1][C:2]1[C:11]2[C:6](=[C:7]([Br:15])[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=2)[N:5]=[C:4]([OH:16])[N:3]=1.S(=O)(=O)(O)N.N[CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1>>[Br:15][C:7]1[CH:8]=[C:9]([N+:12]([O-:14])=[O:13])[CH:10]=[C:11]2[C:6]=1[N:5]=[C:4]([OH:16])[N:3]=[C:2]2[NH:1][CH2:23][CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][N:29]([CH3:32])[CH2:28][CH2:27]1

Participants

4

Reactant 3

HCID 5987Sulfamic AcidHCID 783281-(3-Aminopropyl)-4-methylpiperazineHCID 178508998HCID 178508998, compound

Product 1

HCID 178480875HCID 178480875, compoundYield 40%

Procedure

A mixture of 4-amino-8-bromo-6-nitro-quinazolin-2-ol (24.1 mg, 0.0845 mmol), sulfamic acid (16.4 mg, 0.169 mmol) and 1-(3-aminopropyl)-4-methylpiperazine (1 ml) was heated at reflux for 7 h. The cooled reaction mixture was poured into 10 ml ice water. The resulting precipitate was collected and purified by preparative HPLC. 19.2 mg product was obtained. Yield: 40%; 1H NMR (500 MHz, DMSO-d6): δ 1.91521–1.95482 (m, 2H), 2.78103(s, 8H), 3.16555(b, 4H), 8.68221–8.68666(d, J=2.225 Hz, 1H), 9.10824–9.11291(d, J=2.335 Hz, 1H); ESI-MS: 425, 427 (M++1)

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 h
  3. customThe cooled reaction mixture
  4. customThe resulting precipitate was collected
  5. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-af1de62f16fe4f08805f0414feda03d7
Source dataset
uspto-grants-2007_04
Patent number
US07208493B2

Reaction notes

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