4-Morpholinecarbonyl chloride → HCID 178455389, compound

HRID 715581Notes

Reaction equation

HRID 715581 reaction equation
[Si:1]([O:8][C@H:9]1[C@H:13]2[O:14][CH2:15][C@@H:16]([O:17][C:18]3[N:40]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:21]4=[N:22][C:23]([C:27]5[CH:32]=[CH:31][C:30]([C@@H:33]6[CH2:38][CH2:37][C@H:36]([OH:39])[CH2:35][CH2:34]6)=[CH:29][CH:28]=5)=[C:24]([Cl:26])[CH:25]=[C:20]4[N:19]=3)[C@H:12]2[O:11][CH2:10]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[N:49]1([C:55](Cl)=[O:56])[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1>N1C=CC=CC=1>[N:49]1([C:55]([O:39][C@H:36]2[CH2:37][CH2:38][C@@H:33]([C:30]3[CH:31]=[CH:32][C:27]([C:23]4[N:22]=[C:21]5[N:40]([CH2:41][O:42][CH2:43][CH2:44][Si:45]([CH3:48])([CH3:47])[CH3:46])[C:18]([O:17][C@@H:16]6[CH2:15][O:14][C@@H:13]7[C@H:9]([O:8][Si:1]([C:4]([CH3:6])([CH3:7])[CH3:5])([CH3:3])[CH3:2])[CH2:10][O:11][C@H:12]67)=[N:19][C:20]5=[CH:25][C:24]=4[Cl:26])=[CH:28][CH:29]=3)[CH2:34][CH2:35]2)=[O:56])[CH2:54][CH2:53][O:52][CH2:51][CH2:50]1

Participants

4

Reactant 2

HCID 848104-Morpholinecarbonyl chloride4×HCID 178455385HCID 178455385, compound

Product 1

HCID 178455389HCID 178455389, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

(cis)-4-(4-(2-((3R,3aR,6R,6aS)-6-(tert-Butyldimethylsilyloxy)hexahydrofuro[3,2-b]furan-3-yloxy)-6-chloro-3-((2-(trimethylsilyl)ethoxy)methyl)-3H-imidazo[4,5-b]pyridin-5-yl)phenyl)cyclohexanol (50 mg) is dissolved in pyridine (1 mL), treated with morpholine-4-carbonyl chloride (25 μL) and stirred for 6 hours at 50° C. Morpholine-4-carbonyl chloride (75 μL) is added and the mixture is stirred for 12 hours at 70° C. Morpholine-4-carbonyl chloride (75 μL) is added and the mixture is stirred for 6 hours at 70° C. Again morpholine-4-carbonyl chloride (250 μL) is added and the mixture is stirred for 12 hours at 70° C. The mixture is partitioned between ethylacetate and hydrochloric acid (1 M). The organic phase is dried (MgSO4) and concentrated. The crude product is used directly in the next step.

Workup

  1. stirringthe mixture is stirred for 12 hours at 70° C
  2. stirringthe mixture is stirred for 6 hours at 70° C
  3. stirringthe mixture is stirred for 12 hours at 70° C
  4. customThe mixture is partitioned between ethylacetate and hydrochloric acid (1 M)
  5. dry with materialThe organic phase is dried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8b05aba43b194e88a25a710a91fc384c
Source dataset
uspto-grants-2015_11
Patent number
US09187477B2

Reaction notes

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