Hydrochloric Acid → HCID 86639692, compound

HRID 1426153Notes

Reaction equation

HRID 1426153 reaction equation
C([O:8][C:9]1[C:10]([NH:23][C:24]2[S:25][CH:26]=[C:27]([CH3:29])[N:28]=2)=[N:11][CH:12]=[C:13]([S:15][CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[CH:14]=1)C1C=CC=CC=1.[ClH:30].NCCS.Cl>>[ClH:30].[ClH:30].[CH3:29][C:27]1[N:28]=[C:24]([NH:23][C:10]2[C:9]([OH:8])=[CH:14][C:13]([S:15][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=3)=[CH:12][N:11]=2)[S:25][CH:26]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 9082Cysteamine HydrochlorideHCID 16660507HCID 16660507, compound

Product 1

HCID 86639692HCID 86639692, compoundYield 95%

Procedure

A 250 mL round-bottomed flask was charged with 3-(benzyloxy)-N-(4-methylthiazol-2-yl)-5-(pyridin-2-ylmethylthio)pyridin-2-amine (prepared in Example 46, 6.6 g, 16 mmol), 2-aminoethanethiol hydrochloride (2.7 g, 24 mmol), and 6M HCl (125 mL). The reaction was heated to reflux for 3 hours. The reaction was concentrated on rotary evaporator to about 40 mL and the resultant solids were removed by filtration. The filtrate was further concentrated and the resultant solids were removed by filtration. This procedure was repeated. The solids were combined to afford the title compound (4.6 g, 73% yield) as a white solid. 1H NMR (DMSO-d6) δ 11.63 (bs, 1H), 8.75 (m, 1H), 8.32 (td, 1H), 7.82 (d, 1H), 7.77 (m, 2H), 7.35 (d, 1H), 6.92 (d, 1H), 4.50 (s, 2H), 2.34 (s, 3H). Mass spectrum (apci) m/z=331.1 (M+H-2HCl).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 3 hours
  3. concentrationThe reaction was concentrated on rotary evaporator to about 40 mL
  4. customthe resultant solids were removed by filtration
  5. concentrationThe filtrate was further concentrated
  6. customthe resultant solids were removed by filtration

Sources & evidence

ORD record
ord-4351b451f67e4da0b7d293938320f1c8
Source dataset
uspto-grants-2015_01
Patent number
US08933077B2

Reaction notes

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