Diisopropylethylamine → (1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(S)-tetrahydro-pyran-3-yl-amine

HRID 1257661Notes

Reaction equation

HRID 1257661 reaction equation
Cl.[O:2]1[CH2:7][CH2:6][CH2:5][C@H:4]([NH2:8])[CH2:3]1.C(N(CC)C(C)C)(C)C.[C:18]1([S:24]([N:27]2[C:31]3=[N:32][CH:33]=[C:34]([N+:37]([O-:39])=[O:38])[C:35](Cl)=[C:30]3[CH:29]=[CH:28]2)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>>[C:18]1([S:24]([N:27]2[C:31]3=[N:32][CH:33]=[C:34]([N+:37]([O-:39])=[O:38])[C:35]([NH:8][C@H:4]4[CH2:5][CH2:6][CH2:7][O:2][CH2:3]4)=[C:30]3[CH:29]=[CH:28]2)(=[O:25])=[O:26])[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 583947741-(benzenesulfonyl)-4-chloro-5-nitro-1H-pyrrolo(2,3-b)pyridineHCID 60145922(3S)-oxan-3-amine hydrochloride

Product 1

HCID 67345277(1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(S)-tetrahydro-pyran-3-yl-amineYield 95.7%

Conditions

Temperature
75 °C

Procedure

(S)-(Tetrahydro-pyran-3-yl)amine hydrochloride (40.7 g, 296.09 mmol) and N,N-diisopropylethylamine (130 mL, 760 mmol) were added to a solution of 1-Benzenesulfonyl-4-chloro-5-nitro-1H-pyrrolo[2,3-b]pyridine (100.0 g, 296.09 mmol) in ispropanol (1.0 L). The mixture was stirred at an internal temperature of 75° C. for 4 hours. The mixture was then allowed to cool down slowly and left still overnight. The resulting solid was collected by filtration and washed with cold isopropanol. The solid was then dried in a vacuum oven for 24 h to afford 114.0 g (95.7%) of (1-Benzenesulfonyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-yl)-(S)-tetrahydro-pyran-3-yl-amine as a yellow solid. LCMS (Method D, ESI): RT=1.63 min, m+H=403.2; 1H NMR (400 MHz, DMSO) δ 9.21 (d, J=8.1 Hz, 1H), 8.92 (s, 1H), 8.13 (d, J=7.8 Hz, 2H), 7.77 (dt, J=25.1, 10.9 Hz, 2H), 7.66 (t, J=7.7 Hz, 2H), 7.02 (d, J=4.1 Hz, 1H), 4.28 (s, 1H), 3.88-3.65 (m, 3H), 3.56 (t, J=8.9 Hz, 1H), 2.00 (t, J=11.5 Hz, 1H), 1.93-1.63 (m, 2H), 1.53 (dd, J=9.4, 4.2 Hz, 1H), 1.28 (t, J=6.9 Hz, 1H).

Workup

  1. temperatureto cool down slowly
  2. waitleft still overnight
  3. filtrationThe resulting solid was collected by filtration
  4. washwashed with cold isopropanol
  5. customThe solid was then dried in a vacuum oven for 24 h

Sources & evidence

ORD record
ord-7a912c1b37344b878dcc83a89b3df2b6
Source dataset
uspto-grants-2013_06
Patent number
US08461328B2

Reaction notes

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