Hydrazine hydrate (1:1) → HCID 178464653, compound

HRID 1396062Notes

Reaction equation

HRID 1396062 reaction equation
[CH2:1]1[C:5]2([CH2:9][CH2:8][CH2:7][CH2:6]2)[CH:4]=[N:3][N:2]1[C:10]([NH:33][CH2:34][CH3:35])=[N:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH2:21][N:22]2C(=O)C3C(=CC=CC=3)C2=O)=[CH:17][CH:16]=1)(=[O:14])=[O:13].O.NN>CCO>[NH2:22][CH2:21][C:18]1[CH:17]=[CH:16][C:15]([S:12]([N:11]=[C:10]([N:2]2[N:3]=[CH:4][C:5]3([CH2:9][CH2:8][CH2:7][CH2:6]3)[CH2:1]2)[NH:33][CH2:34][CH3:35])(=[O:13])=[O:14])=[CH:20][CH:19]=1

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 178464651HCID 178464651, compound

Product 1

HCID 178464653HCID 178464653, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2.51 g N-[(2,3-Diaza-spiro[4.4]non-3-en-2-yl)-ethylamino-methylene]-4-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-benzenesulfonamide was taken up in 50 mL EtOH. After addition of 0.70 mL hydrazine hydrate, the mixture was refluxed for 2 h. After cooling to room temperature, the formed precipitate was filtered off. The filtrate was concentrated, and the residue was triturated with DCM. The solids were filtered off, and the filtrate was evaporated to dryness to give 1.20 g (67%) of 4-Aminomethyl-N-[(2,3-diaza-spiro[4.4]non-3-en-2-yl)-ethylamino-methylene]benzenesulfonamide as a red oil. 1H NMR (400 MHz, CDCl3) δ 1.14 (t, J=7.22 Hz, 3H), 1.59-1.83 (m, 8H), 3.46 (q, 2H), 3.82 (br.s., 2H), 3.92 (br.s., 2H), 6.82 (s, 1H), 7.40 (d, J=8.13 Hz, 2H), 7.88 (d, J=8.13 Hz, 2H) [NH2 & guanidine NH invisible].

Workup

  1. temperaturethe mixture was refluxed for 2 h
  2. filtrationthe formed precipitate was filtered off
  3. concentrationThe filtrate was concentrated
  4. customthe residue was triturated with DCM
  5. filtrationThe solids were filtered off
  6. customthe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-cc2e9f04ea1f42e4a68c7e2d252e3a1d
Source dataset
uspto-grants-2014_12
Patent number
US08901108B2

Reaction notes

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